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Synthesis 2000; 2000(13): 1894-1906
DOI: 10.1055/s-2000-8224
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Synthetic Studies on Azadirachtin: An Efficient Asymmetric Synthesis of the Highly Functionalized Tricyclic Decalin Part of Azadirachtin

Yuuko Yamamoto* , Jun Ishihara, Naoki Kanoh, 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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The detailed examination of intramolecular Diels - Alder reactions of several structurally related trienes led to construction of the desired tricyclic decalin moiety of azadirachtin with the α-hydroxyl groups at C1 and C3 as the oxygenated substituent at C8 in the naturally occurring form in good yields.

azadirachtin - insect antifeedant - decalin - cyclic carbonate - intramolecular Diels - Alder reaction