Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

Christopher D. Vanderwal; David A. Vosburg; Sven Weiler; Erik J. Sorensen

doi:10.1021/ol990723r

Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

Christopher D. Vanderwal, David A. Vosburg, Sven Weiler, Erik J. Sorensen

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

44 Scopus citations

Abstract

(Matrix presented) WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B. Our work features a chemoselective palladium-catalyzed cross-coupling of two advanced building blocks and an uncommon Claisen-like cyclization.

Original language	English (US)
Pages (from-to)	645-648
Number of pages	4
Journal	Organic letters
Volume	1
Issue number	4
DOIs	https://doi.org/10.1021/ol990723r
State	Published - Aug 26 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol990723r

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title = "Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis",

abstract = "(Matrix presented) WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B. Our work features a chemoselective palladium-catalyzed cross-coupling of two advanced building blocks and an uncommon Claisen-like cyclization.",

author = "Vanderwal, {Christopher D.} and Vosburg, {David A.} and Sven Weiler and Sorensen, {Erik J.}",

year = "1999",

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doi = "10.1021/ol990723r",

language = "English (US)",

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journal = "Organic letters",

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T1 - Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

AU - Vanderwal, Christopher D.

AU - Vosburg, David A.

AU - Weiler, Sven

AU - Sorensen, Erik J.

PY - 1999/8/26

Y1 - 1999/8/26

N2 - (Matrix presented) WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B. Our work features a chemoselective palladium-catalyzed cross-coupling of two advanced building blocks and an uncommon Claisen-like cyclization.

AB - (Matrix presented) WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B. Our work features a chemoselective palladium-catalyzed cross-coupling of two advanced building blocks and an uncommon Claisen-like cyclization.

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JO - Organic letters

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ER -

Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

Abstract

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