Photomediated Transformation of Salannin, a Tetranortriterpenoid from Azadirachta indica A. Juss

Photomediated Transformation of Salannin, a Tetranortriterpenoid from Azadirachta indica A. Juss

Photolysis of Salannin (1), an important bioactive compound from Azadirachta indica A.Juss (Neem), affords Δ17-isosalanninolide (2), a hitherto unknown compound, along with isosalanninolide (3) and salanninolide (4). A probable mechanism has been suggested. While the mechanism of formation of 2 i...

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Bibliographic Details
Main Authors: V. Kasinath, N. D. Pradeep Singh, Geetha Gopalakrishnan
Format: Article
Language:English
Published: MDPI AG 2001-05-01
Series:Molecules
Subjects:
Azadirachta indica
Salannin
cycloaddition
sigmatropic shift
antifeedant
Online Access:http://www.mdpi.com/1420-3049/6/6/551/
Description
Summary:Photolysis of Salannin (1), an important bioactive compound from Azadirachta indica A.Juss (Neem), affords Δ17-isosalanninolide (2), a hitherto unknown compound, along with isosalanninolide (3) and salanninolide (4). A probable mechanism has been suggested. While the mechanism of formation of 2 involves both a [4+2] cycloaddition and a [1,3] sigmatropic shift in the furan and D-rings, respectively, formation of 3 and 4 involves the decomposition of an ozonoide-like peroxide intermediate.
ISSN:1420-3049

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