CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA INDICA (Part 3) REACTIONS ON THE C-22,23 ENOL ETHER DOUBLE BOND OF AZADIRACHTIN AND CONVERSION TO 22,23-DIHYDRO-23-&β-METHOXYAZADIRACHTIN.
Azadirachtin (1) can be converted to the natural product 22,23-dihydro-23β-methoxyazadirachtin (2) via selective bromomethoxylation of the C-22,23 enol ether double bond and tri-n-butyltin hydride reduction; the corresponding acetic acid adduct on pyrolysis affords (1) in high yield.The antifeedant effects of the addition compounds were assessed.
Ley, Steven V.,Anderson, James C.,Blaney, Wally M.,Lidert, Zev,Morgan, E. David,et al.