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

Type
Article
Authors
Mukherjee, Herschel
McDougal, Nolan T.
Virgil, Scott C.
Stoltz, Brian M.
KAUST Grant Number
K US-11-006-02
Date
2011-03-04

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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.
Citation
Mukherjee H, McDougal NT, Virgil SC, Stoltz BM (2011) A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B. Organic Letters 13: 825–827. Available: http://dx.doi.org/10.1021/ol102669z.
Sponsors
This publication is based on work supported by Award No. K US-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (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.
Publisher
American Chemical Society (ACS)
Journal
Organic Letters
ISSN
1523-7060
1523-7052
DOI
10.1021/ol102669z
PubMed ID
21271716
PubMed Central ID
PMC3045637
Handle URI
http://hdl.handle.net/10754/597227
Collections
Publications Acknowledging KAUST Support