Abstract
Oxidative methoxylation of 8,17-isopropylidenedioxy derivative of lambertianic acid methyl ester with N-chlorobenzenesulfonamide in methanol, followed by hydrogenation over Raney nickel, gave rise to a 2,5-dimethoxytetrahydrofuran fragment which was converted into N-substituted pyrrole ring by the action of amines in acetic acid. The subsequent removal of the acetonide protection and periodate cleavage of the diols thus formed resulted in the formation of 17-nor-8-oxo derivatives, and the latter underwent smooth cyclization to decahydronaphtho[1,2-g]indoles in acid medium.
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