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

Abstract

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.

Keywords

• Azadirachta indica
• Salannin
• cycloaddition
• sigmatropic shift
• antifeedant