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

Org Lett. 2009 Jun 18;11(12):2531-4. doi: 10.1021/ol900769d.

Authors

Hiroyoshi Takamura¹, Shigetoshi Kikuchi, Yuichi Nakamura, Yuji Yamagami, Takayuki Kishi, Isao Kadota, Yoshinori Yamamoto

Affiliation

¹ Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tushimanaka, Okayama 700-8530, Japan.

PMID: 19441795
DOI: 10.1021/ol900769d

Abstract

A total synthesis of brevenal is described. The pentacyclic ether core was constructed by the intramolecular allylation of alpha-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry
Molecular Structure
Stereoisomerism
Thiopental / analogs & derivatives*
Thiopental / chemical synthesis
Thiopental / chemistry

Substances

Ethers, Cyclic
thiobutabarbital
Thiopental