Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations

Authors
Villar, F Equey, O Renaud, P
Citation
F. Villar et al., Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations, ORG LETT, 2(8), 2000, pp. 1061-1064
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
8
Year of publication
2000
Pages
1061 - 1064
Database
ISI
SICI code
1523-7060(20000420)2:8<1061:DO1ARC>2.0.ZU;2-7
Abstract
Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork rad ical cyclizations is reported. The stereochemistry of the cyclization is co ntrolled by the acetal center. Excellent stereocontrol at C(4) and C(5) of the newly formed tetrahydrofuran rings is observed. Use of a chiral auxilia ry allows the preparation of enantiomerically pure material. The utility of this method has been demonstrated by achieving a short synthesis of (+)-el danolide, the pheromone of the male African sugarcane stem borer Eldana sac charina.