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Org Lett

Title:		"Highly efficient, enantioselective synthesis of (+)-grandisol from a C2-symmetric bis(alpha,beta-butenolide)"
Author(s):		de March P; Figueredo M; Font J; Raya J;
Address:		"Departament de Quimica, Universitat Autonoma de Barcelona, Bellaterra, Spain"
Journal Title:		Org Lett
Year:		2000
Volume:		2
Issue:		2
Page Number:		163 - 165
DOI:		10.1021/ol991261k
ISSN/ISBN:		1523-7060 (Print) 1523-7052 (Linking)
Abstract:		"[reaction: see text] A new, very efficient, enantioselective synthesis of the sexual attracting insect pheromone (+)-grandisol has been developed, in which the key step is the double [2 + 2] photocycloaddition of ethylene to a bis(alpha,beta-butenolide) readily available from D-mannitol. The C2 symmetry of the substrate and the appropriate protection of the central diol unit are the crucial features for the high diastereofacial discrimination during the cycloaddition process"
Keywords:		Mannitol/chemistry Sex Attractants/chemical synthesis/chemistry Stereoisomerism Terpenes/chemical synthesis/*chemistry;
Notes:		"Medlinede March, P Figueredo, M Font, J Raya, J eng Research Support, Non-U.S. Gov't 2000/05/18 Org Lett. 2000 Jan 27; 2(2):163-5. doi: 10.1021/ol991261k"