title: Highly efficient, enantioselective synthesis of (+)-grandisol from a C2-symmetric bis(alpha,beta-butenolide).
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.
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona, Bellaterra, Spain.
authors.forename: P
authors.initials: P
authors.lastname: de March
authors.forename: M
authors.initials: M
authors.lastname: Figueredo
authors.forename: J
authors.initials: J
authors.lastname: Font
authors.forename: J
authors.initials: J
authors.lastname: Raya
mesh_terms: D008353:Mannitol / Q000737:chemistry; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D012724:Sex Attractants; D013729:Terpenes; D008353:Mannitol; C013009:grandisol