Catalytic Enantioselective Synthesis of Cephalotaxine via Asymmetric Tsuji Allylation

来源 :中国化学会第十三届全国有机合成化学学术研讨会 | 被引量 : 0次 | 上传用户:chenghongminghao
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  Cephalotaxine (CET) is the parent member of a group of Cephalotaxus alkaloids1 and its absolute configuration (3S,4S,5R) was confirmed by X-ray analysis of the corresponding p-bromobenzoate.2 Among all naturally occurring ester derivatives of CET,homoharringtonine represents the most effective anticancer ingredient and was approved as an adult orphan-drug for the treatment of chronic myeloid leukemia by the FDA in 2012.Asymmetric synthesis of CET has attracted considerable attention.1 However,reported method mainly used chiral compounds as starting materials or employed chiral auxiliaries to control the diastereoselectivity.Herein,we report that enantioselective formal synthesis of CET was achieved via a catalytic asymmetric Tsuji allylation3 as key step for construction of the quaternary stereogenic center at C5 position.Routine transformations4 easily gave the (-)-Cephalotaxine in 93% ee.
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