(+)(S)(Z)-14-methyl-8-hexadecen-1-ol (I) was prepd. from (+)(S)-EtCHMeCH2CH2CH:CH2 (II) in a series of reactions. Thus, II was subjected to hydroboration-bromination, coupled with HC≡CLi, and lithiated, coupled with 7-iodo-1-heptyl 2-tetrahydropyranyl ether, and hydrolyzed to give (+)(S)-EtCHMe(CH2)4C≡C(CH2)7OH (III); the selective hydrogenation of III gave I. 1-Decyne was converted to (Z)-Me(CH2)7CH:CH(CH2)5CO2Me by lithiation, coupling with 6-iodo-1-hexyl 2-tetrahydropyranyl ether, hydrolysis, selective hydrogenation, oxidn., and esterification by CH2N2.
Insect pheromones - syntheses of chiral and achiral components of the sex pheromones of dermestid beetles of the genus Trogoderma
ROSSI, RENZO;CARPITA, ADRIANO
1977-01-01
Abstract
(+)(S)(Z)-14-methyl-8-hexadecen-1-ol (I) was prepd. from (+)(S)-EtCHMeCH2CH2CH:CH2 (II) in a series of reactions. Thus, II was subjected to hydroboration-bromination, coupled with HC≡CLi, and lithiated, coupled with 7-iodo-1-heptyl 2-tetrahydropyranyl ether, and hydrolyzed to give (+)(S)-EtCHMe(CH2)4C≡C(CH2)7OH (III); the selective hydrogenation of III gave I. 1-Decyne was converted to (Z)-Me(CH2)7CH:CH(CH2)5CO2Me by lithiation, coupling with 6-iodo-1-hexyl 2-tetrahydropyranyl ether, hydrolysis, selective hydrogenation, oxidn., and esterification by CH2N2.File in questo prodotto:
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