Synthesis of (-)-bullatacin: The enantiomer of a potent, antitumor, 4-hydroxylated, Annonaceous acetogenin

Thomas R. Hoye; Paul R. Hanson

doi:10.1016/S0040-4039(00)60671-8

Synthesis of (-)-bullatacin: The enantiomer of a potent, antitumor, 4-hydroxylated, Annonaceous acetogenin

Thomas R. Hoye
, Paul R. Hanson

Research output: Contribution to journal › Article › peer-review

81 Scopus citations

Abstract

Synthesis of the title compound represents the first construction of any of these potent, antitumor Annonaceous acetogenins with the entire relative stereochemistry in place. Palladium(0)-mediated crossed diyne coupling and the use of three, natural, α-hydroxy acids as the origin of all absolute stereochemistry highlight this flexible approach that sets the stage for access to structural analogs for further study.

Original language	English (US)
Pages (from-to)	5043-5046
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(00)60671-8
State	Published - Aug 6 1993

Bibliographical note

Funding Information:
This investigation was supported by grant GM-34492 awarded by the DHHS.

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

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10.1016/S0040-4039(00)60671-8

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abstract = "Synthesis of the title compound represents the first construction of any of these potent, antitumor Annonaceous acetogenins with the entire relative stereochemistry in place. Palladium(0)-mediated crossed diyne coupling and the use of three, natural, α-hydroxy acids as the origin of all absolute stereochemistry highlight this flexible approach that sets the stage for access to structural analogs for further study.",

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AB - Synthesis of the title compound represents the first construction of any of these potent, antitumor Annonaceous acetogenins with the entire relative stereochemistry in place. Palladium(0)-mediated crossed diyne coupling and the use of three, natural, α-hydroxy acids as the origin of all absolute stereochemistry highlight this flexible approach that sets the stage for access to structural analogs for further study.

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Synthesis of (-)-bullatacin: The enantiomer of a potent, antitumor, 4-hydroxylated, Annonaceous acetogenin

Abstract

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