Alkaloid synthesis via intramolecular ene reactions. 1. Application to (.+-.)-crinane
GE Keck, RR Webb
Index: Keck,G.E.; Webb,R.R. Journal of the American Chemical Society, 1981 , vol. 103, p. 3173
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Citation Number: 50
Abstract
Abstract: A general approach to the cis-fused octahydroindole skeleton of representative Amaryllidaceae alkaloids is described. A key feature of the approach is the intramolecular ene reaction of an acylnitroso olefin to give ene product 12, corresponding formally to annulation of a five-membered N-containing ring onto a six-membered carbocycle. The total synthesis of dl-crinane which contains the basic octahydroindole nucleus is described. ...
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