Tetrahedron

Studies on the synthesis of strychnos indole alkaloids: Introduction of the functionalized one-carbon substituent at C-16

M Alvarez, R Lavilla, C Roure, E Cabot, J Bosch

Index: Alvarez, Mercedes; Lavilla, Rodolfo; Roure, Cristina; Cabot, Eulalia; Bosch, Joan Tetrahedron, 1987 , vol. 43, # 11 p. 2513 - 2522

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Citation Number: 6

Abstract

A synthetic way for the construction of the tetracyclic 1, 2, 3, 4, 5, 6-hexabydro-1, 5- methanoazocino [4, 3-b] indo1e system I, having a methoxycarbonyl substituent at the C-6 position, is reported. The synthesis implies methoxycarbonylation of the Interannular methylene carbon of an appropriate 2-(4-pyridylmethyl) indole, followed by alkylation of the pyridine nitrogen, catalytic hydrogenation and, finally, oxidative cyclization of the resulting ...