Glenn C Micalizio

Summary

Affiliation: Dartmouth Medical School
Country: USA

Publications

  1. pmc Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols
    Dexi Yang
    Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA
    Chem Commun (Camb) 49:8857-9. 2013
  2. pmc Synthesis of the C1-C26 hexacyclic subunit of pectenotoxin 2
    Ozora Kubo
    Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA
    Org Lett 14:5748-51. 2012
  3. pmc Concerning the potential reversibility of carbometalation in alkoxide-directed Ti(Oi-Pr)4-mediated reductive cross-coupling of homoallylic alcohols with aromatic imines
    Masayuki Takahashi
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, FL, USA
    Chem Commun (Camb) 46:3336-8. 2010
  4. pmc Convergent and stereospecific synthesis of complex skipped polyenes and polyunsaturated fatty acids
    Todd K Macklin
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way 3A2, Jupiter, Florida 33458, USA
    Nat Chem 2:638-43. 2010
  5. pmc Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation
    Stephen N Greszler
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 134:2766-74. 2012
  6. pmc Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols
    Daniel P Canterbury
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 132:7602-4. 2010
  7. pmc Convergent and stereodivergent synthesis of complex 1-aza-7-oxabicyclo[2.2.1]heptanes
    Dexi Yang
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 133:9216-9. 2011
  8. pmc Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols
    Shuhei Umemura
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    Org Lett 11:5402-5. 2009
  9. pmc Total synthesis of lehualide B by allylic alcohol-alkyne reductive cross-coupling
    Valer Jeso
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 132:11422-4. 2010
  10. doi request reprint Convergent synthesis and discovery of a natural product-inspired paralog-selective Hsp90 inhibitor
    Valer Jeso
    Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA
    Org Lett 13:5108-11. 2011

Collaborators

  • Masayuki Takahashi
  • Gregory S Walker
  • Dexi Yang
  • Valer Jeso
  • Todd K Macklin
  • Michael A Tarselli
  • Daniel P Canterbury
  • Xiaohai Li
  • Claudio Aquino
  • Mohosin Sarkar
  • Michael D Cameron
  • Ozora Kubo
  • Stephen N Greszler
  • Peter S Diez
  • Lark J Perez
  • Ming Z Chen
  • Shuhei Umemura
  • Justin K Belardi
  • Mika Nakashige
  • Haruki Mizoguchi
  • Raman Sharma
  • Scott Heyward
  • Xiayun Cheng
  • Bruce D Pascal
  • Thomas Kodadek
  • Caitlin Steckler
  • Michael J Chalmers
  • Holly A Reichard
  • Alex K Brasher
  • Lisa Cherry
  • Chad E Groer
  • Kirsten M Raehal
  • Laura M Bohn
  • Subhas Chandra Pan
  • John M Streicher
  • Philip V LoGrasso
  • Martin McLaughlin
  • Heidi L Shimp

Detail Information

Publications23

  1. pmc Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols
    Dexi Yang
    Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA
    Chem Commun (Camb) 49:8857-9. 2013
    ..This fundamental property has been employed to realize highly selective asymmetric coupling reactions with allylic alcohols that proceed by dynamic kinetic resolution. ..
  2. pmc Synthesis of the C1-C26 hexacyclic subunit of pectenotoxin 2
    Ozora Kubo
    Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA
    Org Lett 14:5748-51. 2012
    ..Preparation of the C1-C14 AB spriroketal-containing subunit employs a recently developed metallacycle-mediated reductive cross-coupling between a TMS-alkyne and a terminal alkene...
  3. pmc Concerning the potential reversibility of carbometalation in alkoxide-directed Ti(Oi-Pr)4-mediated reductive cross-coupling of homoallylic alcohols with aromatic imines
    Masayuki Takahashi
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, FL, USA
    Chem Commun (Camb) 46:3336-8. 2010
    ..No evidence could be found for olefin exchange in preformed azatitanacyclopentanes--an observation that is consistent with a model based on kinetically controlled selective carbometalation...
  4. pmc Convergent and stereospecific synthesis of complex skipped polyenes and polyunsaturated fatty acids
    Todd K Macklin
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way 3A2, Jupiter, Florida 33458, USA
    Nat Chem 2:638-43. 2010
    ..We also demonstrate the significance of the present bond construction by preparing substituted and stereodefined polyunsaturated synthetic fatty acids...
  5. pmc Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation
    Stephen N Greszler
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 134:2766-74. 2012
    ..Overall, the reaction proceeds with exquisite stereochemical control and defines a convenient, convergent, and enantiospecific entry to fused carbocycles of great potential value in target-oriented synthesis and medicinal chemistry...
  6. pmc Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols
    Daniel P Canterbury
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 132:7602-4. 2010
    ..Overall, the chemistry defines a three-component coupling process for the union of two homoallylic alcohol-based substrates with trimethylsilylacetylene...
  7. pmc Convergent and stereodivergent synthesis of complex 1-aza-7-oxabicyclo[2.2.1]heptanes
    Dexi Yang
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 133:9216-9. 2011
    ....
  8. pmc Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols
    Shuhei Umemura
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    Org Lett 11:5402-5. 2009
    ....
  9. pmc Total synthesis of lehualide B by allylic alcohol-alkyne reductive cross-coupling
    Valer Jeso
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 132:11422-4. 2010
    ..The challenging C12-C16 bis-trisubstituted 1,4-diene was installed with a complex reductive cross-coupling reaction between a preformed Ti-alkyne complex and a pyrone-containing allylic alcohol...
  10. doi request reprint Convergent synthesis and discovery of a natural product-inspired paralog-selective Hsp90 inhibitor
    Valer Jeso
    Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA
    Org Lett 13:5108-11. 2011
    ....
  11. pmc Convergent synthesis of piperidines by the union of conjugated alkynes with imines: a unique regioselective bond construction for heterocycle synthesis
    Ming Z Chen
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    Org Lett 11:4982-5. 2009
    ..Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings...
  12. pmc Aliphatic imines in titanium-mediated reductive cross-coupling: unique reactivity of Ti(O-i-Pr)4/n-BuLi
    Michael A Tarselli
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    Org Lett 11:4596-9. 2009
    ..The success of these studies was enabled by a unique reactivity profile of Ti(IV) isopropoxide/n-BuLi compared to well-known Ti(IV) isopropoxide/RMgX systems...
  13. pmc A convergent stereoselective synthesis of quinolizidines and indolizidines: chemoselective coupling of 2-hydroxymethyl-substituted allylic silanes with imines
    Dexi Yang
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 131:17548-9. 2009
    ..Overall, highly substituted heterocycles that contain three stereogenic centers and up to four fused rings can be accessed in two steps from relatively simple coupling partners...
  14. pmc Synthesis of alkaloid (-)-205B via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition
    Dexi Yang
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 134:15237-40. 2012
    ..Overall, the synthesis is asymmetric, concise, and highly stereoselective-features which point to the potential future utility of these chemical methods in natural product synthesis and medicinal chemistry...
  15. doi request reprint Stereoselective synthesis of trisubstituted (E,E)-1,3-dienes by the site-selective reductive cross-coupling of internal alkynes with terminal alkynes: a fragment coupling reaction for natural product synthesis
    Lark J Perez
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA
    J Org Chem 74:7211-9. 2009
    ....
  16. pmc Synthesis of angularly substituted trans-fused hydroindanes by convergent coupling of acyclic precursors
    Valer Jeso
    Department of Chemistry, Burke Laboratory, Dartmouth College, Hanover, New Hampshire 03755, United States
    J Am Chem Soc 136:8209-12. 2014
    ..Several examples are given to demonstrate the compatibility of this reaction with substrates bearing aromatic and aliphatic substituents, and an empirical model is presented to accompany the stereochemical observations. ..
  17. pmc Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols
    Masayuki Takahashi
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, 130 Scripps Way 3A2, Jupiter, FL 33458, USA
    Angew Chem Int Ed Engl 48:3648-52. 2009
    ..The process proceeds with net allylic transposition without the intermediacy of allylic organometallic reagents. Two stereodefined centers and a geometrically defined di- or trisubstituted alkene are forged with high selectivity...
  18. doi request reprint Total synthesis and structure elucidation of (+)-phorbasin C
    Todd K Macklin
    Department of Chemistry, Yale University, New Haven, Connecticut 06520 8107, USA
    J Am Chem Soc 131:1392-3. 2009
    ..The first total synthesis and structure elucidation of a member of the phorbasin class of natural products is described...
  19. pmc Characterization of T-5 N-oxide formation as the first highly selective measure of CYP3A5 activity
    Xiaohai Li
    Department of Molecular Therapeutics, Scripps Research Institute, Jupiter, Florida M D C, X L Celsis In Vitro Technologies, Baltimore Maryland S H Department of Chemistry, Dartmouth College, Hanover, New Hampshire V J, G C M, Pharmacokinetics, Dynamics, and Metabolism Department, Pfizer Global Research and Development, Groton, Connecticut G S W, R S
    Drug Metab Dispos 42:334-42. 2014
    ..Formation of T-5 N-oxide highly correlates with the CYP3A5 genotype and CYP3A5 expression levels in human liver microsomes and human hepatocytes. ..
  20. pmc Chemoselective reductive cross-coupling of 1,5-diene-3-ols with alkynes: a facile entry to stereodefined skipped trienes
    Peter S Diez
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA
    J Am Chem Soc 132:9576-8. 2010
    ..The control of site selectivity in functionalization of the substituted diene is a central feature of this complex fragment union reaction...
  21. doi request reprint Synthesis of conolidine, a potent non-opioid analgesic for tonic and persistent pain
    Michael A Tarselli
    Department of Chemistry, The Scripps Research Institute, Jupiter, Florida, USA
    Nat Chem 3:449-53. 2011
    ....
  22. doi request reprint Decoding split and pool combinatorial libraries with electron-transfer dissociation tandem mass spectrometry
    Mohosin Sarkar
    Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, FL 33458, USA
    J Am Soc Mass Spectrom 24:1026-36. 2013
    ..In addition, we have created "Hit-Find," a software program that allows users to generate libraries in silico. The user can then search all possible members of the chemical library for those that fall within a user-defined mass error...
  23. pmc Conversion of allylic alcohols to stereodefined trisubstituted alkenes: a complementary process to the Claisen rearrangement
    Justin K Belardi
    Department of Chemistry, Yale University, New Haven, Connecticut 06520 8107, USA
    J Am Chem Soc 130:16870-2. 2008
    ..Overall, the reaction sequence described is stereochemically complementary to related Claisen rearrangement reactions--processes that typically deliver the stereoisomeric trisubstituted alkene containing products...