Novel formal synthesis of cephalotaxine via a facile Friedel-Crafts cyclization

被引：37
作者：
Li, Wei-Dong Z. [1 ]
Wang, Xin-Wei
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 07期
关键词：
D O I：
10.1021/ol070024b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 = H-2) were observed.
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页码：1211 / 1214
页数：4
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