Application of the B-alkyl suzuki-miyaura cross-coupling reaction to the stereoselective synthesis of analogues of (3S)-oxidosqualene

Johan M Winne; Bing Guang; Jo D'Herde; Pierre J De Clercq

doi:10.1021/ol061962z

Application of the B-alkyl suzuki-miyaura cross-coupling reaction to the stereoselective synthesis of analogues of (3S)-oxidosqualene

Org Lett. 2006 Oct 12;8(21):4815-8. doi: 10.1021/ol061962z.

Authors

Johan M Winne¹, Bing Guang, Jo D'Herde, Pierre J De Clercq

Affiliation

¹ Department of Organic Chemistry, Ghent University, Krijgslaan 281/S4, B-9000 Ghent, Belgium.

PMID: 17020310
DOI: 10.1021/ol061962z

Abstract

[reaction: see text] A general method is described for the direct and stereoselective synthesis of epoxypolyenes via Suzuki-Miyaura cross-coupling reaction of 1-iodoalkenes with B-alkylboron compounds. It allows for the straightforward and convergent assembly of compounds that are structurally similar to (3S)-oxidosqualene, an important intermediate in steroid biosynthesis.

Publication types

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

MeSH terms

Catalysis
Molecular Structure
Squalene* / analogs & derivatives
Squalene* / chemical synthesis
Squalene* / chemistry
Stereoisomerism

Substances

oxidosqualene
Squalene