Journal of Organic Chemistry p. 5321 - 5326 (1983)
Update date:2022-08-17
Topics:
Hiranuma, Sayoko
Shibata, Misako
Hudlicky, Tomas
The alkaloid ester homoharringtonine (2) was synthesized stereospecifically via the Reformatsky reaction of methyl α-bromoacetate with cephalotaxyl pyruvate (16) obtained by esterification of cephalotaxine with acid chloride derived from 15.The preparations of 2 and its 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 Reformatsky reaction leading to 2 and 13 are advanced.
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