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Synthesis of a limonoid, azadiradione

✍ Scribed by E.J. Corey; Robert W. Hahl

Book ID
104229544
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
239 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Azadiradione 1 has been synthesized stereoselectively from trans, trans-farnesol. Since the elucidation of the structure of limonin in 1960,l a large number of naturally occurring substances of the limonoid family have been isolated and characterized structurally. Described herein is a synthesis of azadiradione

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Synthesis of 13Ξ²-analogs of azadiradione
Synthesis of 13Ξ²-analogs of azadiradione
✍ Alfonso FernΓ‘ndez-Mateos; Ana M. LΓ³pez Barba; Eva MartΓ­n de la Nava; Gustavo Pas πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 529 KB

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.