Total synthesis of the tylophora alkaloids rusplinone, 13aα-secoantofine, and antofine using a multicatalytic oxidative aminochlorocarbonylation/Friedel-Crafts reaction

被引：25
作者：
Ambrosini, Lisa M. [1 ]
Cernak, Tim A. [1 ]
Lambert, Tristan H. [1 ]
机构：
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
来源：
TETRAHEDRON | 2010年 / 66卷 / 26期
关键词：
Oxidative carbonylation; Multicatalysis; Tylophora alkaloids; Antofine; Palladium; INTRAMOLECULAR ALKOXYPALLADATION CARBONYLATION; ASYMMETRIC TOTAL-SYNTHESIS; QUINOLIZIDINE ALKALOIDS; PHENANTHROINDOLIZIDINE ALKALOIDS; ALKOXY-CARBONYLATION; CYTOTOXIC ACTIVITY; CRYPTOPLEURINE; INDOLIZIDINE; (-)-ANTOFINE; CATALYSIS;
D O I：
10.1016/j.tet.2010.03.021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rapid synthetic approach to the tylophora alkaloids antofine and 13a alpha-secoantofine is presented that makes use of a multicatalytic oxidative aminochlorocarbonylation/Friedel-Crafts reaction as the key step. This reaction, along with a one-pot, three-step telescoped process offers a three or four-pot sequence to access the title compounds in high overall yield. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4882 / 4887
页数：6
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