The Journal of Organic Chemistry

Synthesis of enantiomerically pure hydrinden-2-ones and benz [e] inden-2-ones via asymmetric alkylations of chiral bicyclic lactams

L Snyder, AI Meyers

Index: Snyder, Lawrence; Meyers, A. I. Journal of Organic Chemistry, 1993 , vol. 58, # 26 p. 7507 - 7515

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Citation Number: 25

Abstract

A route to the titled compounds in> 99% ee was achieved from sequential diastereoselective alkylations of chiral, nonracemic bicyclic lactams 6 and 15. An intramolecular addition of the organolithium species derived from 17a-c and 28a-d gave, after hydrolysis, diketones 25a-c and 30a-d, which were cyclized to the titled compounds 4a-c and 31a-d. As an example of the versatility of this method, the ABC ring system of the triterpene stelliferin A, isolated ...