Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations
[formula: see text] Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations is reported. The stereochemistry of the cyclization is controlled by the acetal center. Excellent stereocontrol at C(4) and C(5) of the newly formed tetrahydrofuran rings is observed. Use of a chiral auxiliary allows the preparation of enantiomerically pure material. The utility of this method has been demonstrated by achieving a short synthesis of (+)-eldanolide, the pheromone of the male African sugarcane stem borer Eldana saccharina.
Villar
F
Universite de Fribourg, Institut de Chimie Organique, Perolles, Switzerland.
Equey
O
Renaud
P