Biomimetic synthesis of the shimalactones

Vladimir Sofiyev; Gabriel Navarro; Dirk Trauner

doi:10.1021/ol702806v

Biomimetic synthesis of the shimalactones

Vladimir Sofiyev, Gabriel Navarro, Dirk Trauner

Chemistry

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

Abstract

A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl β-ketolactone and a Stille coupling/8π-6π electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.

Original language	English (US)
Pages (from-to)	149-152
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	1
DOIs	https://doi.org/10.1021/ol702806v
State	Published - Jan 3 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol702806v

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abstract = "A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl β-ketolactone and a Stille coupling/8π-6π electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.",

author = "Vladimir Sofiyev and Gabriel Navarro and Dirk Trauner",

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N2 - A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl β-ketolactone and a Stille coupling/8π-6π electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.

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Biomimetic synthesis of the shimalactones

Abstract

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