A Highly Convergent and Biomimetic Total Synthesis of Portentol

Bichu Cheng; Dirk Trauner

doi:10.1021/jacs.5b10009

A Highly Convergent and Biomimetic Total Synthesis of Portentol

Bichu Cheng, Dirk Trauner

Chemistry

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

Abstract

An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.

Original language	English (US)
Pages (from-to)	13800-13803
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	43
DOIs	https://doi.org/10.1021/jacs.5b10009
State	Published - Nov 4 2015

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.5b10009

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abstract = "An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.",

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A Highly Convergent and Biomimetic Total Synthesis of Portentol

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