Timothy J Donohoe

Summary

Affiliation: University of Oxford
Country: UK

Publications

  1. pmc Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization
    Ben S Pilgrim
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U K, and GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, U K
    Org Lett 15:6190-3. 2013
  2. doi request reprint Interplay of cascade oxidative cyclization and hydride shifts in the synthesis of the ABC spiroketal ring system of pectenotoxin-4
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Angew Chem Int Ed Engl 52:2491-4. 2013
  3. doi request reprint Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
    Org Lett 14:5460-3. 2012
  4. doi request reprint Natural product synthesis as a challenging test of newly developed methodology
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Commun (Camb) 48:11924-38. 2012
  5. doi request reprint A Lewis acid promoted oxidative cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    J Org Chem 74:6394-7. 2009
  6. pmc An expedient route to substituted furans via olefin cross-metathesis
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Oxford, OX1 3TA UK
    Proc Natl Acad Sci U S A 107:3373-6. 2010
  7. doi request reprint New modes for the osmium-catalyzed oxidative cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    Org Lett 12:1060-3. 2010
  8. doi request reprint Regioselective nucleophilic addition to pyridinium salts: a new route to substituted dihydropyridones
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 11:5562-5. 2009
  9. doi request reprint Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    J Am Chem Soc 131:12854-61. 2009
  10. ncbi request reprint Osmium-mediated oxidative cyclizations: a study into the range of initiators that facilitate cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Asian J 4:1237-47. 2009

Collaborators

Detail Information

Publications63

  1. pmc Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization
    Ben S Pilgrim
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U K, and GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, U K
    Org Lett 15:6190-3. 2013
    ..tert-Butyl cyanoacetate participated in a similar protocol; after functionalization and decarboxylation, 3-amino-4-alkyl isoquinolines were prepared in high yield. ..
  2. doi request reprint Interplay of cascade oxidative cyclization and hydride shifts in the synthesis of the ABC spiroketal ring system of pectenotoxin-4
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Angew Chem Int Ed Engl 52:2491-4. 2013
    ..The resulting sequence has been used in a synthesis of the C1-16 fragment of the naturally occurring antitumor agent pectenotoxin-4...
  3. doi request reprint Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
    Org Lett 14:5460-3. 2012
    ..Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO(4) catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde...
  4. doi request reprint Natural product synthesis as a challenging test of newly developed methodology
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Commun (Camb) 48:11924-38. 2012
    ..This article describes the examination of several synthetic methodologies that have been developed in our laboratories, by application to the construction of a variety of natural product targets...
  5. doi request reprint A Lewis acid promoted oxidative cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    J Org Chem 74:6394-7. 2009
    ..2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions...
  6. pmc An expedient route to substituted furans via olefin cross-metathesis
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Oxford, OX1 3TA UK
    Proc Natl Acad Sci U S A 107:3373-6. 2010
    ..These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes...
  7. doi request reprint New modes for the osmium-catalyzed oxidative cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    Org Lett 12:1060-3. 2010
    ..Moreover, the cyclization of bis-homoallylic amines bearing an exocyclic chelating group is shown to be a complementary method for trans-pyrrolidine formation...
  8. doi request reprint Regioselective nucleophilic addition to pyridinium salts: a new route to substituted dihydropyridones
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 11:5562-5. 2009
    ..The dihydropyridone products can be further manipulated in many ways using standard transformations...
  9. doi request reprint Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    J Am Chem Soc 131:12854-61. 2009
    ..A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin...
  10. ncbi request reprint Osmium-mediated oxidative cyclizations: a study into the range of initiators that facilitate cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Asian J 4:1237-47. 2009
    ..Moreover, routes to enantiopure starting materials are described, which give enantiopure products upon cyclization. Catalyst loadings of as low as one mol percent have been successfully employed for this transformation...
  11. doi request reprint Synthesis of (+)-DGDP and (-)-7-epialexine
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Org Biomol Chem 6:3896-8. 2008
    ..The partial reduction of electron deficient pyrroles is an extremely versatile method that allows us to prepare substituted pyrrolidines and pyrrolizidines with trans-diol stereochemistry on the five membered ring...
  12. doi request reprint Synthesis of (-)-(Z)-deoxypukalide
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Angew Chem Int Ed Engl 47:7314-6. 2008
  13. doi request reprint Flexible strategy for the synthesis of pyrrolizidine alkaloids
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    Org Lett 10:3615-8. 2008
    ..Finally, this work allowed assignment of the absolute stereochemistry of 2,3,7-triepiaustraline and hyacinthacine A 7...
  14. doi request reprint Ring-closing metathesis: novel routes to aromatic heterocycles
    Timothy J Donohoe
    Chemistry Research Laboratory, University of Oxford, Oxford, OX1 3TA UK
    Chemistry 14:5716-26. 2008
    ..The importance of heteroaromatic motifs in medicinal chemistry and biology, as well as the efficiency and wealth of metathesis transformations, have resulted in significant success in this rapidly developing area...
  15. ncbi request reprint Substituted pyrroles via olefin cross-metathesis
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Org Lett 12:4094-7. 2010
    ..The value of this chemistry is demonstrated by its application to the tetrasubstituted pyrrole subunit of Atorvastatin...
  16. doi request reprint A novel oxidative cyclisation onto vinyl silanes
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Commun (Camb) 46:7310-2. 2010
    ..The scope of this reaction can also be extended beyond 1,2-diols and applied to the cyclisation of α-hydroxy-sulfonamides and α-hydroxy-amides...
  17. doi request reprint Synthesis of 2,4,6-trisubstituted pyridines via an olefin cross-metathesis/Heck-cyclisation-elimination sequence
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Commun (Camb) 47:10611-3. 2011
    ..Subsequent one-pot cyclisation/elimination provides an operationally simple, catalytic and convergent synthesis of 2,4,6-trisubstituted pyridines...
  18. doi request reprint Olefin cross-metathesis for the synthesis of heteroaromatic compounds
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Org Biomol Chem 10:1322-8. 2012
    ..This approach allows a convergent union of simple, functionalised, three- to four-carbon olefinic core building blocks, to generate furans, pyrroles and pyridines with a high degree of control of substitution pattern in the product...
  19. doi request reprint Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK OX1 3TA
    Org Biomol Chem 10:1093-101. 2012
    ..The alkene starting materials are themselves readily accessible using many different and well-established approaches, and allow access to a variety of heterocycles with excellent yields and regioselectivity...
  20. doi request reprint Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesis
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    J Am Chem Soc 133:16418-21. 2011
    ..The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment...
  21. doi request reprint The influence of exocyclic stereochemistry on the tethered aminohydroxylation reaction
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Asian J 6:3214-22. 2011
    ..Furthermore, an "inside alkoxy" model is employed to rationalize the sense and degree of stereoselectivity observed in these systems...
  22. doi request reprint Exerting control over the acyloin reaction
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
    Chem Commun (Camb) 47:5849-51. 2011
    ..By linking two esters via their oxygen atoms, it was possible to perform crossed acyloin reactions between two different ester functionalities and display a high degree of preference for an intramolecular coupling process...
  23. doi request reprint Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
    Org Lett 13:2074-7. 2011
    ..The heterocyclic products contain ample functionality for further elaboration reactions and subsequent derivatization...
  24. doi request reprint Heteroaromatic synthesis via olefin cross-metathesis: entry to polysubstituted pyridines
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Oxford, UK
    Org Lett 13:1036-9. 2011
    ..High levels of regiocontrol, short reaction sequences, and facile substituent variation are all notable aspects of this methodology...
  25. doi request reprint Recent developments in methodology for the direct oxyamination of olefins
    Timothy J Donohoe
    Department of Chemistry, Chemical Research Laboratory, University of Oxford, UK
    Chemistry 17:58-76. 2011
    ..There are still many challenges to be overcome and, herein, we also outline the areas that are ripe for further development and which bode well for the future...
  26. doi request reprint Olefin cross-metathesis-based approaches to furans: procedures for the preparation of di- and trisubstituted variants
    Timothy J Donohoe
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK
    Nat Protoc 5:2005-10. 2010
    ..The reaction procedure given for the formation of the 2,5-disubstituted furan (option A) takes ∼26.5 h to complete. The procedure described for the formation of the 2,3,5-trisubstituted furan (option B) takes ∼52.5 h...
  27. doi request reprint Pyridine-N-oxide as a mild reoxidant which transforms osmium-catalyzed oxidative cyclization
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Angew Chem Int Ed Engl 47:2872-5. 2008
  28. doi request reprint Hydride shift generated oxonium ions: evidence for mechanism and intramolecular trapping experiments to form trans THF derivatives
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    Angew Chem Int Ed Engl 47:2869-71. 2008
  29. ncbi request reprint Ring-closing metathesis as a basis for the construction of aromatic compounds
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Angew Chem Int Ed Engl 45:2664-70. 2006
    ....
  30. ncbi request reprint The ammonia-free partial reduction of substituted pyridinium salts
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UKOX1 3TA
    Org Biomol Chem 4:1071-84. 2006
    ....
  31. ncbi request reprint N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reaction
    Timothy J Donohoe
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, UK
    J Am Chem Soc 128:2514-5. 2006
    ..In addition to providing aminohydroxylation products in good yields, the catalyst loadings can be reduced to just 1 mol % osmium. Moreover, for the first time, homoallylic alcohols are now viable substrates for the TA reaction...
  32. ncbi request reprint A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline
    Timothy J Donohoe
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    J Org Chem 70:7297-304. 2005
    ..A first synthesis of hyacinthacine A1 is described that also confirmed the structure of the natural product, and a short stereoselective synthesis of 1-epiaustraline is also discussed in detail...
  33. ncbi request reprint Oxidative cyclization of diols derived from 1,5-dienes: formation of enantiopure cis-tetrahydrofurans by using catalytic osmium tetroxide; formal synthesis of (+)-cis-solamin
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK
    Angew Chem Int Ed Engl 44:4766-8. 2005
  34. ncbi request reprint Concise and enantioselective synthesis of the aminocyclitol core of hygromycin A
    Timothy J Donohoe
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 7:1275-7. 2005
    ..This tactic allowed efficient differentiation of otherwise equivalent hydroxyl groups and allowed us to complete the synthesis in short order (14 steps) and excellent overall yield (12%)...
  35. ncbi request reprint Partial reduction of pyridinium salts as a versatile route to dihydropyridones
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 7:435-7. 2005
    ..Each position on the dihydropyridone ring is then accessible using standard synthetic manipulations...
  36. ncbi request reprint An efficient synthesis of lactacystin beta-lactone
    Timothy J Donohoe
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
    Angew Chem Int Ed Engl 43:2293-6. 2004
  37. ncbi request reprint Synthesis of (+/-)-secosyrin 1 and a formal synthesis of (-)-secosyrin 1
    Timothy J Donohoe
    Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
    Org Lett 6:465-7. 2004
    ..Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary...
  38. ncbi request reprint Synthesis of enantiopure dihydropyranones: aldol-based ring expansion of dihydrofurans
    Timothy J Donohoe
    Dyson Perrins Laboratory, South Parks Road, Oxford OX1 3QY, UK
    Org Lett 4:3059-62. 2002
    ..This sequence has ample flexibility built into it, either by the use of different electrophiles during reductive alkylation or by subsequent derivatization of the dihydropyranone after ring expansion...
  39. ncbi request reprint New osmium-based reagent for the dihydroxylation of alkenes
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
    J Org Chem 71:4481-9. 2006
    ....
  40. ncbi request reprint An enzymatic approach to the desymmetrization of disubstituted pyrrolines
    Timothy J Donohoe
    Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
    J Org Chem 71:6298-301. 2006
    ..The enzyme reaction precursors are formed easily from two readily available substituted pyrroles using both ammonia (Na/NH3) and ammonia-free (Li/DBB) Birch reduction conditions...
  41. ncbi request reprint Partial reduction of pyrroles: application to natural product synthesis
    Timothy J Donohoe
    Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    Chem Rec 7:180-90. 2007
    ..This leads to formation of both enantiomers of 2,2- and 2,5-disubstituted N-Boc pyrrolines in excellent ee and yields...
  42. ncbi request reprint A concise and efficient synthesis of (-)-allosamizoline
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 9:5509-11. 2007
    ..Allosamizoline was prepared in a total of 13 steps and 22% overall yield...
  43. ncbi request reprint A metathesis-based approach to the synthesis of 2-pyridones and pyridines
    Timothy J Donohoe
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom
    Org Lett 10:285-8. 2008
    ..This mild and novel approach to six-membered heteroaromatic compounds then provides access to a wide variety of substituted pyridines in excellent overall yield...
  44. ncbi request reprint Tethered aminohydroxylation: dramatic improvements to the process
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 9:1725-8. 2007
    ..Acyclic homoallylic alcohols were substrates considered too unreactive for effective use in the tethered aminohydroxylation reaction; improved reaction conditions mean that they have now become viable substrates for oxidation...
  45. ncbi request reprint Synthesis of the pyrrolidinone core of KSM-2690 B
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U K
    Org Lett 9:421-4. 2007
    ..An ammonia-free Birch reductive aldol reaction utilizing acetaldehyde is one of the key steps, together with a ruthenium-catalyzed alkene isomerization reaction...
  46. ncbi request reprint Stereoselective synthesis of pyrrolidines: catalytic oxidative cyclizations mediated by osmium
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Angew Chem Int Ed Engl 45:8025-8. 2006
  47. ncbi request reprint Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK
    J Am Chem Soc 128:13704-5. 2006
    ..The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total...
  48. ncbi request reprint The partial reduction of electron-deficient pyrroles: procedures describing both Birch (Li/NH3) and ammonia-free (Li/DBB) conditions
    Timothy J Donohoe
    Chemistry Research Laboratory, University of Oxford, Oxford, UK
    Nat Protoc 2:1888-95. 2007
    ..5 h to complete. Those described for the ammonia-free reductions, procedure B and procedure C, can be expected to take approximately 33 and 8 h, respectively...
  49. ncbi request reprint Enantioselective partial reduction of 2,5-disubstituted pyrroles via a chiral protonation approach
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 6:3055-8. 2004
    ..An enantiomeric excess of up to 74% was achieved using (-)-ephedrine and related analogues as chiral proton sources. The pyrroline product obtained could be recrystallized to give enantiomerically pure material...
  50. ncbi request reprint A metathesis-based approach to the synthesis of furans
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U K
    Org Lett 9:953-6. 2007
    ..reaction: see text]..
  51. ncbi request reprint Utility of the ammonia-free Birch reduction of electron-deficient pyrroles: total synthesis of the 20s proteasome inhibitor, clasto-lactacystin beta-lactone
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK
    Chemistry 11:4227-38. 2005
    ..The final synthesis proceeds in just 13 steps and in 15 % overall yield making it an extremely efficient route to this valuable compound...
  52. pmc Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis
    Timothy J Donohoe
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, United Kingdom
    J Org Chem 78:12338-50. 2013
    ..Furthermore, assessment of a number of chiral ligands in a challenging asymmetric Suzuki-Miyaura cross-coupling reaction has enabled enantioenriched (up to 42% ee) synthetic streptonigrin intermediates to be prepared for the first time. ..
  53. pmc De novo synthesis of multisubstituted aryl amines using alkene cross metathesis
    Matthew R Tatton
    Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, U K
    Org Lett 16:1920-3. 2014
    ..This de novo arene synthesis yields nonclassical substitution patterns in a regioselective and predictable approach that is compatible with several functional groups. ..
  54. pmc Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom
    Proc Natl Acad Sci U S A 109:11605-8. 2012
    ..This powerful route to polysubstituted isoquinolines, which is not limited to electron rich moieties, also allows rapid access to analogues of biologically active compounds...
  55. pmc Tethered aminohydroxylation: synthesis of the β-amino acid of microsclerodermins A and B
    Robert D C Pullin
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, U K
    Org Lett 15:5492-5. 2013
    ..The route includes late-stage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render the synthesis applicable to other microsclerodermins. ..
  56. ncbi request reprint A concise total synthesis of (+/-)-1-epiaustraline
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    Org Lett 6:2003-6. 2004
    ..The C1 and C2 stereocenters were set through an OsO(4)-catalyzed dihydroxylation...
  57. doi request reprint Osmium-free direct syn-dihydroxylation of alkenes
    Carole J R Bataille
    Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
    Chem Soc Rev 40:114-28. 2011
    ..It is the intent of the following tutorial review to present a concise summary of the main methods used to prepare syn-diol fragments directly from alkene precursors, and that do not make use of osmium oxo complexes as catalysts...
  58. ncbi request reprint Flexibility in the partial reduction of 2,5-disubstituted pyrroles: application to the synthesis of DMDP
    Timothy J Donohoe
    Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, United Kingdom
    Org Lett 5:999-1002. 2003
    ..Finally, this method was applied to a synthesis of the naturally occurring glycosidase inhibitor DMDP...
  59. ncbi request reprint Trichloro-oxazolines as activated donors for aminosugar coupling
    Timothy J Donohoe
    Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK
    Org Lett 5:4995-8. 2003
    ..Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions. [reaction: see text]..
  60. doi request reprint Rhodium-catalyzed ketone methylation using methanol under mild conditions: formation of α-branched products
    Louis K M Chan
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA UK
    Angew Chem Int Ed Engl 53:761-5. 2014
    ..Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a sequential one-pot iridium- and rhodium-catalyzed process. ..
  61. doi request reprint Osmium-catalyzed oxidative cyclization of dienes and their derivatives
    Ben S Pilgrim
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK
    J Org Chem 78:2149-67. 2013
    ..Pleasingly, the catalytic oxidative cyclization has proved itself to be an efficient and functional group tolerant process that was pivotal to the completion of several natural product syntheses...
  62. ncbi request reprint Tethered Aminohydroxylation (TA) Reaction of Amides
    Timothy J Donohoe
    Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA
    Org Lett 11:2305-7. 2009
    ..The levels of diastereoselectivity that were observed for substituents at both the allylic and homallylic position bode well for the use of stereoselective TA reactions in organic synthesis...
  63. ncbi request reprint Dehydrogenation of cyclic thioethers bound to a [Rh(diphosphine)]+ fragment
    Romaeo Dallanegra
    Department of Chemistry, University of Oxford, Oxford, OX1 3TA, UK
    Dalton Trans 40:6626-8. 2011
    ..The metal-promoted dehydrogenation of cyclic thioethers S(C(5)H(9))(R) (R = C(5)H(9), Ph) to give the corresponding cycloalkenes, S(C(5)H(7))(R), using the [Rh{Ph(2)P(CH(2))(3)PPh(2)}](+) fragment is reported...