(+)(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

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.
Rossi, Renzo; Carpita, Adriano
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/2184
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