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

Handle URI:
http://hdl.handle.net/10754/597227
Title:
A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B
Authors:
Mukherjee, Herschel; McDougal, Nolan T.; Virgil, Scott C.; Stoltz, Brian M.
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.
Publisher:
American Chemical Society (ACS)
Journal:
Organic Letters
KAUST Grant Number:
K US-11-006-02
Issue Date:
4-Mar-2011
DOI:
10.1021/ol102669z
PubMed ID:
21271716
PubMed Central ID:
PMC3045637
Type:
Article
ISSN:
1523-7060; 1523-7052
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.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorMukherjee, Herschelen
dc.contributor.authorMcDougal, Nolan T.en
dc.contributor.authorVirgil, Scott C.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-25T12:28:25Zen
dc.date.available2016-02-25T12:28:25Zen
dc.date.issued2011-03-04en
dc.identifier.citationMukherjee 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.en
dc.identifier.issn1523-7060en
dc.identifier.issn1523-7052en
dc.identifier.pmid21271716en
dc.identifier.doi10.1021/ol102669zen
dc.identifier.urihttp://hdl.handle.net/10754/597227en
dc.description.abstractA 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.en
dc.description.sponsorshipThis 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.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleA Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran Ben
dc.typeArticleen
dc.identifier.journalOrganic Lettersen
dc.identifier.pmcidPMC3045637en
dc.contributor.institutionThe Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, Pasadena, California 91125, USA.en
kaust.grant.numberK US-11-006-02en

Related articles on PubMed

All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.