Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin

Takehiro Fukuzaki; Satoshi Kobayashi; Takamasa Hibi; Yohei Ikuma; Jun Ishihara; Naoki Kanoh; Akio Murai

doi:10.1021/ol026260y

Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin

Org Lett. 2002 Aug 22;4(17):2877-80. doi: 10.1021/ol026260y.

Authors

Takehiro Fukuzaki¹, Satoshi Kobayashi, Takamasa Hibi, Yohei Ikuma, Jun Ishihara, Naoki Kanoh, Akio Murai

Affiliation

¹ Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

PMID: 12182578
DOI: 10.1021/ol026260y

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids
Esters
Insecticides / chemical synthesis
Limonins / chemical synthesis*
Silanes
Stereoisomerism

Substances

Carboxylic Acids
Esters
Insecticides
Limonins
Silanes
dichlorodimethylsilane
azadirachtin