Total synthesis of brevenal

Hiroyoshi Takamura; Shigetoshi Kikuchi; Yuichi Nakamura; Yuji Yamagami; Takayuki Kishi; Isao Kadota; Yoshinori Yamamoto

doi:10.1021/ol900769d

Total synthesis of brevenal

Hiroyoshi Takamura, Shigetoshi Kikuchi, Yuichi Nakamura, Yuji Yamagami, Takayuki Kishi, Isao Kadota, Yoshinori Yamamoto

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

53 Citations (Scopus)

Abstract

A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of α-acetoxy ether and subsequent ring - closing metathesis. Both of the diene side chains were introduced by Wittig olefination and a Horner - Wadsworth - Emmons reaction, respectively, in a highly stereoselective manner.

Original language	English
Pages (from-to)	2531-2534
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	12
DOIs	https://doi.org/10.1021/ol900769d
Publication status	Published - Jun 18 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Total synthesis of brevenal",

abstract = "A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of α-acetoxy ether and subsequent ring - closing metathesis. Both of the diene side chains were introduced by Wittig olefination and a Horner - Wadsworth - Emmons reaction, respectively, in a highly stereoselective manner.",

author = "Hiroyoshi Takamura and Shigetoshi Kikuchi and Yuichi Nakamura and Yuji Yamagami and Takayuki Kishi and Isao Kadota and Yoshinori Yamamoto",

year = "2009",

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AU - Takamura, Hiroyoshi

AU - Kikuchi, Shigetoshi

AU - Nakamura, Yuichi

AU - Yamagami, Yuji

AU - Kishi, Takayuki

AU - Kadota, Isao

AU - Yamamoto, Yoshinori

PY - 2009/6/18

Y1 - 2009/6/18

N2 - A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of α-acetoxy ether and subsequent ring - closing metathesis. Both of the diene side chains were introduced by Wittig olefination and a Horner - Wadsworth - Emmons reaction, respectively, in a highly stereoselective manner.

AB - A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of α-acetoxy ether and subsequent ring - closing metathesis. Both of the diene side chains were introduced by Wittig olefination and a Horner - Wadsworth - Emmons reaction, respectively, in a highly stereoselective manner.

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