Novel formal synthesis of cephalotaxine via a facile Friedel-Crafts cyclization |
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Authors: | Li Wei-Dong Z Wang Xin-Wei |
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Institution: | State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China. wdli@nankai.edu.cn |
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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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