Total synthesis of brevenal

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)2531-2534
Number of pages4
JournalOrganic Letters
Volume11
Issue number12
DOIs
Publication statusPublished - Jun 18 2009

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Ether
ethers
Allylation
metathesis
dienes
closing
synthesis
rings

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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

Total synthesis of brevenal. / Takamura, Hiroyoshi; Kikuchi, Shigetoshi; Nakamura, Yuichi; Yamagami, Yuji; Kishi, Takayuki; Kadota, Isao; Yamamoto, Yoshinori.

In: Organic Letters, Vol. 11, No. 12, 18.06.2009, p. 2531-2534.

Research output: Contribution to journalArticle

Takamura, H, Kikuchi, S, Nakamura, Y, Yamagami, Y, Kishi, T, Kadota, I & Yamamoto, Y 2009, 'Total synthesis of brevenal', Organic Letters, vol. 11, no. 12, pp. 2531-2534. https://doi.org/10.1021/ol900769d
Takamura H, Kikuchi S, Nakamura Y, Yamagami Y, Kishi T, Kadota I et al. Total synthesis of brevenal. Organic Letters. 2009 Jun 18;11(12):2531-2534. https://doi.org/10.1021/ol900769d
Takamura, Hiroyoshi ; Kikuchi, Shigetoshi ; Nakamura, Yuichi ; Yamagami, Yuji ; Kishi, Takayuki ; Kadota, Isao ; Yamamoto, Yoshinori. / Total synthesis of brevenal. In: Organic Letters. 2009 ; Vol. 11, No. 12. pp. 2531-2534.
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