Chemistry of insect antifeedants from azadirachta indica (part 7): Preparation of an optically pure hydroxyacetal epoxide related to azadirachtin.

✍ Scribed by James C. Anderson; Steven V. Ley

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 255 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97416-1

✦ Synopsis

tion "r" of an opdcally pure hydroxyacetal epoxide (2) as a model cunpound of the potent anti eedant axadimchtin (1) is mported

We wish to report new synthetic studies towards key structural fragments of the potent antifeedant and growth regulator agent amdirachtin (1)2 isolated from the neem tree Azadirachru Mica A. Juss (Meliaceae).

Jn preliminary studies towards the total synthesis of (1) we have developed synthetic sequences to various components of this novel molecule including the substituted decalin units and a dihydrofuranyl acetal fragment.ltl Furthermore, we have shown that simple skeletal structures can mimic the antifeedant activity of the natural product.4 These insect behavioural control substances have some advantages over conventional methods5 and may well tlnd future applications as part of integrated pest management control progmmmes.

Here we discuss the preparation of a hydmxyteuacyclicacetal epoxide (2) as a species encompassing