Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin.
[reaction: see text] Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid framework stereoselectively in good yield.
Fukuzaki
Takehiro
T
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
Kobayashi
Satoshi
S
Hibi
Takamasa
T
Ikuma
Yohei
Y
Ishihara
Jun
J
Kanoh
Naoki
N
Murai
Akio
A
D002264:Carboxylic Acids; D004952:Esters; D007306:Insecticides / Q000138:chemical synthesis; D036701:Limonins / Q000138:chemical synthesis*; D012821:Silanes; D013237:Stereoisomerism
D002264:Carboxylic Acids; D004952:Esters; D007306:Insecticides; D036701:Limonins; D012821:Silanes; C040863:dichlorodimethylsilane; C010329:azadirachtin