Total synthesis of (+)-aspidospermidine: A new strategy for the enantiospecific synthesis of aspidosperma alkaloids

被引:115
作者
Marino, JP [1 ]
Rubio, MB [1 ]
Cao, GF [1 ]
de Dios, A [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ja026357f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new strategy was developed for the enantiospecific synthesis of aspidosperma alkaloids. The key steps involve a novel ketene-lactonization reaction of a chiral vinyl sulfoxide to efficiently set up the quaternary carbon center, and a tandem Michael addition-alkylation reaction sequence to form the polycyclic core structure. This new strategy was employed in the total synthesis of natural product (+)-aspidospermidine. Copyright © 2002 American Chemical Society.
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收藏
页码:13398 / 13399
页数:2
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