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

Herschel Mukherjee; Nolan T. McDougal; Scott C. Virgil; Brian M. Stoltz

doi:10.1021/ol102669z

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

Herschel Mukherjee, Nolan T. McDougal, Scott C. Virgil, Brian M. Stoltz

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52 Scopus citations

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.

Original language	English (US)
Pages (from-to)	825-827
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	5
DOIs	https://doi.org/10.1021/ol102669z
State	Published - Mar 4 2011
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): K US-11-006-02
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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

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.",

author = "Herschel Mukherjee and McDougal, {Nolan T.} and Virgil, {Scott C.} and Stoltz, {Brian M.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): K US-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2011",

month = mar,

day = "4",

doi = "10.1021/ol102669z",

language = "English (US)",

volume = "13",

pages = "825--827",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B

AU - Mukherjee, Herschel

AU - McDougal, Nolan T.

AU - Virgil, Scott C.

AU - Stoltz, Brian M.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): K US-11-006-02 Acknowledgements: 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2011/3/4

Y1 - 2011/3/4

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/597227

UR - https://pubs.acs.org/doi/10.1021/ol102669z

UR - http://www.scopus.com/inward/record.url?scp=79952169657&partnerID=8YFLogxK

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SP - 825

EP - 827

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

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

Abstract

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