Chem. and stereoisomerically pure dendrolasin [I, R = (E)-Q] (Q = Me2C:CHCH2CH2CMe:CHCH2) was prepd. by Grignard reaction of I (R = Br) with (E)-QOHc in the presence of Li2CuCl4, whereas similar reaction of neryl acetate gave 99% stereoisomerically pure I (R = neryl). Moreover, β-farnesene [(E)-QCH2C(:CH2)CH:CH2) and β-springene [(E,E)-CH2:CHC(:CH2)CH2CH2CH:CMeCH2CH2CH:CMeCH2CH2CH:CMe2] were prepd. via coupling of the π-allylnickel halide complex derived from Me2C:CHCH2Br with BrCH2CMe:CHCH2CH2C(:CH2)CH:CH2 (II) or similar reaction of the π-allylnickel complex derived from II with QBr, resp.
Regio- and stereospecific syntheses of achiral terpenoid allomones and pheromone components: dendrolasin, (E)-beta-farnesene, and beta-springene
CARPITA, ADRIANO;ROSSI, RENZO
1984-01-01
Abstract
Chem. and stereoisomerically pure dendrolasin [I, R = (E)-Q] (Q = Me2C:CHCH2CH2CMe:CHCH2) was prepd. by Grignard reaction of I (R = Br) with (E)-QOHc in the presence of Li2CuCl4, whereas similar reaction of neryl acetate gave 99% stereoisomerically pure I (R = neryl). Moreover, β-farnesene [(E)-QCH2C(:CH2)CH:CH2) and β-springene [(E,E)-CH2:CHC(:CH2)CH2CH2CH:CMeCH2CH2CH:CMeCH2CH2CH:CMe2] were prepd. via coupling of the π-allylnickel halide complex derived from Me2C:CHCH2Br with BrCH2CMe:CHCH2CH2C(:CH2)CH:CH2 (II) or similar reaction of the π-allylnickel complex derived from II with QBr, resp.File in questo prodotto:
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