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| Timothy J DonohoeSummaryAffiliation: University of Oxford Country: UK Publications
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Publications
Interplay of cascade oxidative cyclization and hydride shifts in the synthesis of the ABC spiroketal ring system of pectenotoxin-4Timothy 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...- Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin ATimothy 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... - Natural product synthesis as a challenging test of newly developed methodologyTimothy 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... - A Lewis acid promoted oxidative cyclizationTimothy 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... 
An expedient route to substituted furans via olefin cross-metathesisTimothy 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...- New modes for the osmium-catalyzed oxidative cyclizationTimothy 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... - Regioselective nucleophilic addition to pyridinium salts: a new route to substituted dihydropyridonesTimothy 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... - Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticinTimothy 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... - Osmium-mediated oxidative cyclizations: a study into the range of initiators that facilitate cyclizationTimothy 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... - Synthesis of (+)-DGDP and (-)-7-epialexineTimothy 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... 
Synthesis of (-)-(Z)-deoxypukalideTimothy 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- Flexible strategy for the synthesis of pyrrolizidine alkaloidsTimothy 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... - Ring-closing metathesis: novel routes to aromatic heterocyclesTimothy 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... - Substituted pyrroles via olefin cross-metathesisTimothy 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... - A novel oxidative cyclisation onto vinyl silanesTimothy 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... - Olefin cross-metathesis for the synthesis of heteroaromatic compoundsTimothy 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... - Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenesTimothy 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... - Total synthesis of (±)-streptonigrin: de novo construction of a pentasubstituted pyridine using ring-closing metathesisTimothy 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... - The influence of exocyclic stereochemistry on the tethered aminohydroxylation reactionTimothy 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... - Synthesis of 2,4,6-trisubstituted pyridines via an olefin cross-metathesis/Heck-cyclisation-elimination sequenceTimothy 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... - Exerting control over the acyloin reactionTimothy 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... - Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridonesTimothy 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... - Heteroaromatic synthesis via olefin cross-metathesis: entry to polysubstituted pyridinesTimothy 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... - Recent developments in methodology for the direct oxyamination of olefinsTimothy 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... - Olefin cross-metathesis-based approaches to furans: procedures for the preparation of di- and trisubstituted variantsTimothy 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... - Pyridine-N-oxide as a mild reoxidant which transforms osmium-catalyzed oxidative cyclizationTimothy 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 - Hydride shift generated oxonium ions: evidence for mechanism and intramolecular trapping experiments to form trans THF derivativesTimothy 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 - A metathesis-based approach to the synthesis of 2-pyridones and pyridinesTimothy 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... - The ammonia-free partial reduction of substituted pyridinium saltsTimothy J Donohoe
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UKOX1 3TA
Org Biomol Chem 4:1071-84. 2006.... - N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reactionTimothy 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... - A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustralineTimothy 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... - Oxidative cyclization of diols derived from 1,5-dienes: formation of enantiopure cis-tetrahydrofurans by using catalytic osmium tetroxide; formal synthesis of (+)-cis-solaminTimothy J Donohoe
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK
Angew Chem Int Ed Engl 44:4766-8. 2005 - Concise and enantioselective synthesis of the aminocyclitol core of hygromycin ATimothy 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%)... - Partial reduction of pyridinium salts as a versatile route to dihydropyridonesTimothy 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... - An efficient synthesis of lactacystin beta-lactoneTimothy 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 - Synthesis of (+/-)-secosyrin 1 and a formal synthesis of (-)-secosyrin 1Timothy 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... - Synthesis of enantiopure dihydropyranones: aldol-based ring expansion of dihydrofuransTimothy 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... - Ring-closing metathesis as a basis for the construction of aromatic compoundsTimothy 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.... - New osmium-based reagent for the dihydroxylation of alkenesTimothy J Donohoe
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK
J Org Chem 71:4481-9. 2006.... - An enzymatic approach to the desymmetrization of disubstituted pyrrolinesTimothy 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... - A concise and efficient synthesis of (-)-allosamizolineTimothy 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... - The partial reduction of electron-deficient pyrroles: procedures describing both Birch (Li/NH3) and ammonia-free (Li/DBB) conditionsTimothy 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... - Partial reduction of pyrroles: application to natural product synthesisTimothy 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... - Tethered aminohydroxylation: dramatic improvements to the processTimothy 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... - Stereoselective synthesis of pyrrolidines: catalytic oxidative cyclizations mediated by osmiumTimothy 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 - Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmiumTimothy 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... - Synthesis of the pyrrolidinone core of KSM-2690 BTimothy 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... - Enantioselective partial reduction of 2,5-disubstituted pyrroles via a chiral protonation approachTimothy 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... - A metathesis-based approach to the synthesis of furansTimothy 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].. - Utility of the ammonia-free Birch reduction of electron-deficient pyrroles: total synthesis of the 20s proteasome inhibitor, clasto-lactacystin beta-lactoneTimothy 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... - A concise total synthesis of (+/-)-1-epiaustralineTimothy 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... - Osmium-free direct syn-dihydroxylation of alkenesCarole 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... - Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketonesTimothy 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... - Flexibility in the partial reduction of 2,5-disubstituted pyrroles: application to the synthesis of DMDPTimothy 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... - Trichloro-oxazolines as activated donors for aminosugar couplingTimothy 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].. - Osmium-catalyzed oxidative cyclization of dienes and their derivativesBen 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... - Dehydrogenation of cyclic thioethers bound to a [Rh(diphosphine)]+ fragmentRomaeo 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... - Tethered Aminohydroxylation (TA) Reaction of AmidesTimothy 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...