Chemistry of insect antifeedants from Azadirachta indica(part 21): synthesis of model compounds of azadirachtin using a decalin framework as a functional group scaffolding

Abstract

An investigation has been carried out of the synthesis of structural models for the left hand portion of the natural product azadirachtin 1. This work has culminated in a concise and high-yielding route to decalin derivative 2. The significant antifeedant activity shown by this mimic 2 (AI₅₀ at 9.4 ppm) is greater than that of the other analogues synthesised during this study and has led to the synthesis of further mimics 3 and 4.