TOTAL SYNTHESIS OF SCOPINE, PSEUDOSCOPINE, AND NOR-DERIVATIVES

Scopine and pseudoscopine have been synthesised from cyclohepta-3.5-di enol: the initial 1,4-fuctionalisation of the diene is based on a nitr oso-cycloaddition. The use of the N-benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl o r novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso- cycloaddition to 5,6-epoxycyclohepta-1.3-diene is described. Copyright (C) 1996 Else vier Science Ltd.