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  • Title: Novel formal synthesis of cephalotaxine via a facile Friedel-Crafts cyclization.
    Author: Li WD, Wang XW.
    Journal: Org Lett; 2007 Mar 29; 9(7):1211-4. PubMed ID: 17348663.
    Abstract:
    [structure: see text]. A novel formal synthesis of cephalotaxine (CET), the parent structure of the antileukemia Cephalotaxus alkaloids, was achieved via a facile Friedel-Crafts cyclization of the amino (or amido) spiro-cyclopentenone precursor (A) mediated by a protic acid leading to tetracyclic ketone B. A remarkable stereoelectronic effect of the methylenedioxy substituent (R) and an interesting skeletal isomerization of the CET core ring system (B, X = H2) were observed.
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