Tetrahedron

Total synthesis of scopine, pseudoscopine, and nor-derivatives

DE Justice, JR Malpass

Index: Justice, David E.; Malpass, John R. Tetrahedron, 1996 , vol. 52, # 36 p. 11977 - 11994

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Citation Number: 19

Abstract

Scopine and pseudoscopine have been synthesised from cyclohepta-3, 5-dienol; the initial 1, 4-fuctionalisation of the diene is based on a nitroso-cycloaddition. The use of the N- benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl or novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso-cycloaddition to 5, 6-epoxycyclohepta-1, ...