Studies in cephalotaxus alkaloids. Stereospecific total synthesis of homoharringtonine

S Hiranuma, M Shibata, T Hudlicky

Index: Hiranuma, Sayoko; Shibata, Misako; Hudlicky, Tomas Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5321 - 5326

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Citation Number: 26

Abstract

The alkaloid ester homoharringtonine (2) was synthesized stereospecifically via the Reformatsky reaction of methyl a-bromoacetate with cephalotaxyl pyruvate (16) obtained by esterification of cephalotaxine with acid chloride derived from 15. The preparations of 2 and ita unsaturated derivative 13 are described in detail. Possible explanations of the steric requirements in the esterification of cephalotaxine and of the steric outcome of the ...