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

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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

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Takamura, H., Kikuchi, S., Nakamura, Y., Yamagami, Y., Kishi, T., Kadota, I., & Yamamoto, Y. (2009). Total synthesis of brevenal. Organic Letters, 11(12), 2531-2534. https://doi.org/10.1021/ol900769d

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AU - Nakamura, Yuichi

AU - Yamagami, Yuji

AU - Kishi, Takayuki

AU - Kadota, Isao

AU - Yamamoto, Yoshinori

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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.

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Access to Document

10.1021/ol900769d