A new synthetic entry to pentacyclic Strychnos alkaloids. Total synthesis of (.+-.)-tubifolidine,(.+-.)-tubifoline, and (.+-.)-19, 20-dihydroakuammicine
M Amat, A Linares, J Bosch
Index: Amat, Mercedes; Linares, Ana; Bosch, Joan Journal of Organic Chemistry, 1990 , vol. 55, # 26 p. 6299 - 6312
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Citation Number: 81
Abstract
A new strategy for the synthesis of pentacyclic Strychnos alkaloids has been developed. It consists in the closure of the five-membered E ring by cyclization upon the indole 3-position from a suitably N-substituted tetracyclic system embodying rings ABCD of the alkaloids. Attempts to effect the key cyclization either by Pummerer rearrangement of sulfiiylacetamides 4 and 6, from chloroacetamide 12, or from bis (methy1thio) acetamide ...
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