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Synthesis of 13β-analogs of azadiradione

✍ Scribed by Alfonso Fernández-Mateos; Ana M. López Barba; Eva Martín de la Nava; Gustavo Pascual Coca; JoséJ. Pérez Alonso; Ana I. Ramos Silvo; Rosa Rubio González

Book ID
104208074
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
529 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

The synthesis of keto ester 15 related to the limonoid antifeedant azadiradione has been achieved in nine steps starting from hydroxy ester 1. The key steps involve a Nazarov cyclization 6-o10 and a stereoselective epoxy ketone rearrangement to enone 13 -015.

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Synthesis of Insect Antifeedants Related to Azadiradione. -The key step in the synthesis of title compound (IX) are a Nazarov cyclization of the divinyl ketone (IV) with acid and a dyotropic rearrangement of the epoxide (VII). The overall yield of the 8-step reaction is 18%. -(FERNANDEZ MA-