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  • Title: Stereoselective synthesis of (-)-cephalotaxine and C-7 alkylated analogues.
    Author: Planas L, Pérard-Viret J, Royer J.
    Journal: J Org Chem; 2004 Apr 30; 69(9):3087-92. PubMed ID: 15104447.
    Abstract:
    A total asymmetric synthesis of (-)-cephalotaxine is reported. The chemistry of alpha,beta-unsaturated gamma-lactams was used to access the 1-azaspiro[4.4]nonane skeleton in enantiomerically pure form via a stereocontrolled semipinacolic rearrangement of an alpha-hydroxyiminium ion. This spiro compound was transformed into (-)-cephalotaxine without any racemization or epimerization by following the racemic synthesis reported by Kuehne. We thus performed a total synthesis of (-)-cephalotaxine in 98.7% ee with an overall yield of 9.8% over a 16 steps sequence. This synthetic process was adaptable to the access of some alkylated analogues.
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