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Org Lett

Title:		"Desymmetrization of 1,4-dien-3-ols and related compounds via Ueno-Stork radical cyclizations"
Author(s):		Villar F; Equey O; Renaud P;
Address:		"Universite de Fribourg, Institut de Chimie Organique, Perolles, Switzerland"
Journal Title:		Org Lett
Year:		2000
Volume:		2
Issue:		8
Page Number:		1061 - 1064
DOI:		10.1021/ol005613v
ISSN/ISBN:		1523-7052 (Electronic) 1523-7052 (Linking)
Abstract:		"[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"
Keywords:
Notes:		"PubMed-not-MEDLINEVillar, F Equey, O Renaud, P eng 2000/05/11 Org Lett. 2000 Apr 20; 2(8):1061-4. doi: 10.1021/ol005613v"