An Efficient Enantioselective Synthesis of (-)-Serricorole

Von Oppolzer, Wolfgang; Rodriguez, Ines

doi:10.1002/hlca.19930760314

Scientific article

English

An Efficient Enantioselective Synthesis of (-)-Serricorole

ContributorsVon Oppolzer, Wolfgang; Rodriguez, Ines

Published inHelvetica chimica acta, vol. 76, no. 3, p. 1275-1281

Publication date1993

Abstract

The cigarette beetle pheromone (–)-serricorole (1) has been synthesized in 23% overall yield by an eight-step sequence starting from N-propionylsultam 3. The synthesis features asymmetric anti- and syn-aldolizations 3 [RIGHTWARDS ARROW] 4 and 8 [RIGHTWARDS ARROW] 9, a non-destructive N-acylsultam cleavage with lithiated ethylphenylsulfone (10 [RIGHTWARDS ARROW] 12), and the smooth, Ti-mediated cyclization of β-acyloxy-ketone 2 to dihydropyranone 14.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, RODRIGUEZ, Ines. An Efficient Enantioselective Synthesis of (-)-Serricorole. In: Helvetica chimica acta, 1993, vol. 76, n° 3, p. 1275–1281. doi: 10.1002/hlca.19930760314

Article (Published version)

Identifiers

PID : unige:84781
DOI : 10.1002/hlca.19930760314

Journal ISSN0018-019X

503views

2downloads

Creation21/06/2016 16:33:00

First validation21/06/2016 16:33:00

Update time15/03/2023 00:29:19

Status update15/03/2023 00:29:19

Last indexation31/10/2024 03:46:32

Archive ouverte UNIGE

An Efficient Enantioselective Synthesis of (-)-Serricorole

Technical informations