Total synthesis of brevenal.
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.
Takamura
Hiroyoshi
H
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tushimanaka, Okayama 700-8530, Japan.
Kikuchi
Shigetoshi
S
Nakamura
Yuichi
Y
Yamagami
Yuji
Y
Kishi
Takayuki
T
Kadota
Isao
I
Yamamoto
Yoshinori
Y
D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013874:Thiopental / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D004988:Ethers, Cyclic; C004316:thiobutabarbital; D013874:Thiopental