Tetrahedron letters

Transbromination of brominated pyrrole and imidazole derivatives: Synthesis of the C 11 N 5 marine alkaloid stevensine

Y Xu, K Yakushijin, DA Horne

Index: Xu, Ying-Zi; Yakushijin, Kenichi; Horne, David A. Tetrahedron Letters, 1996 , vol. 37, # 45 p. 8121 - 8124

Full Text: HTML

Citation Number: 16

Abstract

The marine sponge alkaloid stevensine (3) has been synthesized from the related C11N5 alkaloid, hymenin (1). The key transformation involves a regioselective protodebromination/ transbromination event of 4′-bromohymenin (2) to install the olefin in 3. Such processes are seldom used for synthetic purposes but appear to be highly applicable to the C11N5 family of marine alkaloids.