Total synthesis of the racemic form of the second juvenile hormone (methyl 12-homojuvenate) from the cecropia silk moth.
Methyl cis-10-epoxy-3,7,11-trimethyl-trans,trans-2,6-tridecadienoate has been stereoselectively synthesized in 12 steps starting from methyl trans-gamma-bromo-beta,beta-dimethylacrylate and 1-acetyl-1-methylcyclopropane. The final product proved to be identical with the second, less abundant juvenile hormone (methyl 12-homojuvenate) isolated from the Cecropia silk moth. The biological activities of the compound were evaluated in various insects.
DEPARTMENT OF CHEMISTRY, STANFORD UNIVERSITY.
W S
WS
Johnson
S F
SF
Campbell
A
A
Krishnakumaran
A S
AS
Meyer