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A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B

Mukherjee, Herschel and McDougal, Nolan T. and Virgil, Scott C. and Stoltz, Brian M. (2011) A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B. Organic Letters, 13 (5). pp. 825-827. ISSN 1523-7060. PMCID PMC3045637. http://resolver.caltech.edu/CaltechAUTHORS:20110201-085102866

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Abstract

A concise asymmetric, formal synthesis of (+)-hamigeran B is reported. A Pd-catalyzed, decarboxylative allylic alkylation, employing a trifluoromethylated derivative of t-BuPHOX, is utilized as the enantioselective step to form the critical quaternary carbon center in excellent yield and enantioselectivity. The product is converted in three steps to a late-stage intermediate previously used in the synthesis of hamigeran B.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol102669zDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol102669zPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3045637/PubMed CentralArticle
Additional Information:© 2011 American Chemical Society. Received December 8, 2010. Publication Date (Web): January 27, 2011. This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIHNIGMS (R01 GM 080269-01), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support and Materia, Inc. for the kind donation of catalyst 8. Dr. Douglas C. Behenna is gratefully acknowledged for assistance in the preparation of the manuscript.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11-006-02
NIHR01 GM 080269-01
Abbott LaboratoriesUNSPECIFIED
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
PubMed Central ID:PMC3045637
Record Number:CaltechAUTHORS:20110201-085102866
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20110201-085102866
Official Citation:A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B Herschel Mukherjee, Nolan T. McDougal, Scott C. Virgil, and Brian M. Stoltz Organic Letters 2011 13 (5), 825-827
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:21943
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:03 Mar 2011 18:54
Last Modified:18 Dec 2014 00:04

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