Tetrahedron

Synthesis of aspidospermidine alkaloids from 1, 2, 3, 4-tetrahydrocarbazole: Total stereoselective synthesis of (±)-18-noraspidospermidine

A Urrutia, JG Rodríguez

Index: Urrutia, Anahi; Rodriguez, J. Gonzalo Tetrahedron, 1999 , vol. 55, # 36 p. 11095 - 11108

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Citation Number: 29

Abstract

The reactivity of the 1, 2, 3, 4-tetrahydrocarbazol-4-one derivatives has been analysed and applied to the synthesis of (±)-18-noraspidospermidine (1b). This was synthesised, starting from 4-(1′, 3′-dioxolan-2′-yl) cyclohexanone which was successively transformed to 3- methyl-3-(3′-nitropropyl)-1, 2, 3, 4-tetrahydrocarbazol-4-one and to the imine tetracycle 13 by means of nickel boride catalyst. The reduction of 13 to the natural cis D ring junction ...