- Journal
- TETRAHEDRON
- Année
- 2006
- Volume
- 62
- Numéro
- 38
- Pages
- 9017-9037
- Mois
- SEP 18
- DOI
- 10.1016/j.tet.2006.07.010
Abstract
Unsaturated sultones have been synthesized from various primary or secondary alkenols by ring-closing metathesis of the corresponding unsaturated sulfonates. By treatment with a strong base, beta,gamma-unsaturated sultones can be metalated and subsequently alkylated with electrophiles. When iodomethylmagnesium chloride was selected as the electrophile, seven-membered ring beta,gamma-unsaturated sultones were converted into homoallylic conjugated (Z)-dienols. This methodology was applied to the racemic synthesis of the originally proposed structure of the marine natural product mycothiazole. (c) 2006 Elsevier Ltd. All rights reserved.