Tetrahedron

On the stereochemistry of the solvolytic c/d ring cleavage of the 1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo [2, 3-a] quinolizine system

MJ Calverley, J Harley-Mason, SA Quarrie…

Index: Calverly, M. J.; Harley-Mason, J.; Quarrie, S. A.; Edwards, P. D. Tetrahedron, 1981 , vol. 37, p. 1547 - 1556

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Citation Number: 10

Abstract

A model sequence for the synthesis of C-mavacurine-type alkaloids is elaborated to demonstrate that substitution at C-12b in the reactions of the amines (4) with cyanogen bromide and methanol (Scheme 6) proceeds with stereospecific inversion of configuration. The same stereospecificity is observed in the analogous reactions of 4, or their O-acetates (5), with benzyl chloroformate and methanol (Scheme 8). To account for the ...