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
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.5b10009

Fingerprint Dive into the research topics of 'A Highly Convergent and Biomimetic Total Synthesis of Portentol'. Together they form a unique fingerprint.

Cite this

@article{147d9c00de444a6db3b5a99f3bdb0a05,

title = "A Highly Convergent and Biomimetic Total Synthesis of Portentol",

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.",

author = "Bichu Cheng and Dirk Trauner",

year = "2015",

month = nov,

day = "4",

doi = "10.1021/jacs.5b10009",

language = "English (US)",

volume = "137",

pages = "13800--13803",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "43",

}

TY - JOUR

T1 - A Highly Convergent and Biomimetic Total Synthesis of Portentol

AU - Cheng, Bichu

AU - Trauner, Dirk

PY - 2015/11/4

Y1 - 2015/11/4

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84953391638&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84953391638&partnerID=8YFLogxK

U2 - 10.1021/jacs.5b10009

DO - 10.1021/jacs.5b10009

M3 - Article

C2 - 26471956

AN - SCOPUS:84953391638

VL - 137

SP - 13800

EP - 13803

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 43

ER -

A Highly Convergent and Biomimetic Total Synthesis of Portentol

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this