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Synthesis 2000; 2000(13): 1878-1893
DOI: 10.1055/s-2000-8223
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Synthetic Studies on Azadirachtin: Asymmetric Synthesis of the Tetracyclic Decalin Part of Azadirachtin

Naoki Kanoh* , Jun Ishihara, Yuuko Yamamoto, Akio Murai
  • *Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, 060-0810, Japan; Fax +81(11)7 06 27 14; E-mail: amurai@sci.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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A synthesis of the tetracyclic decalin part of azadirachtin in the naturally occurring form is described. The key reactions involve the Corey-Bakshi-Shibata (CBS) asymmetric reduction of the ketone, and an intramolecular Diels - Alder (IMDA) reaction.

azadirachtin - insect antifeedant - decalin - CBS asymmetric reduction - intramolecular Diels - Alder reaction