Total synthesis of (.+-.)-methyl homosecodaphniphyllate. A remarkable new tetracyclization reaction

…, MM Hansen, CH Heathcock

Index: Ruggeri, Roger B.; Hansen, Marvin M.; Heathcock, Clayton H. Journal of the American Chemical Society, 1988 , vol. 110, # 26 p. 8734 - 8736

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Citation Number: 70

Abstract

(3) Amide 1 was prepared from 8-valerolactone in two steps in 90% overall yield (1. KOH, benzyl chloride, refluxing toluene; 2. N, N'-carbonyldiimidazole, pyrrolidine). Details will be reported in the full paper.(4) Unsaturated ester 2 was prepared by reduction of 2- (methoxycarbony1) cyclopentanone with NaBH, and elimination of the resulting alcohol with p-toluenesulfonyl chloride and pyridine. See:(a) Rhoads, SJ; Chattopadhyay, JK; Waali, ...