Tetrahedron

Synthesis of bicyclic guanidines from pyrrolidin-2-one

S Louwrier, A Tuynman, H Hiemstra

Index: Louwrier, Saskia; Tuynman, Antonin; Hiemstra, Henk Tetrahedron, 1996 , vol. 52, # 7 p. 2629 - 2646

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Citation Number: 19

Abstract

The syntheses of three bicyclic guanidines as model compounds for the guanidine alkaloid ptilomycalin A are described. The guanidines are prepared from pyrrolidin-2-one via an N- acyliminium ion coupling reaction with silyl enol ethers and a direct guanylation with bis-Boc- thiourea and HgCl2 as the key steps.

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