Concise Asymmetric Synthesis of Kweichowenol A

David B. Konrad; Bilal Kicin; Dirk Trauner

doi:10.1055/s-0037-1610390

Concise Asymmetric Synthesis of Kweichowenol A

David B. Konrad, Bilal Kicin, Dirk Trauner

Chemistry

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

Abstract

An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.

Original language	English (US)
Pages (from-to)	383-386
Number of pages	4
Journal	Synlett
Volume	30
Issue number	4
DOIs	https://doi.org/10.1055/s-0037-1610390
State	Published - 2019

Keywords

Kiyooka aldol
acyclic stereocontrol
asymmetric synthesis
kweichowenol A
natural product synthesis

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0037-1610390

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title = "Concise Asymmetric Synthesis of Kweichowenol A",

abstract = "An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.",

keywords = "Kiyooka aldol, acyclic stereocontrol, asymmetric synthesis, kweichowenol A, natural product synthesis",

author = "Konrad, {David B.} and Bilal Kicin and Dirk Trauner",

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language = "English (US)",

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T1 - Concise Asymmetric Synthesis of Kweichowenol A

AU - Konrad, David B.

AU - Kicin, Bilal

AU - Trauner, Dirk

N1 - Publisher Copyright: © Georg Thieme Verlag.

PY - 2019

Y1 - 2019

N2 - An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.

AB - An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.

KW - Kiyooka aldol

KW - acyclic stereocontrol

KW - asymmetric synthesis

KW - kweichowenol A

KW - natural product synthesis

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SP - 383

EP - 386

JO - Synlett

JF - Synlett

IS - 4

ER -

Concise Asymmetric Synthesis of Kweichowenol A

Abstract

Keywords

ASJC Scopus subject areas

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