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