Synthesis of Demissidine by a Ring Fragmentation 1,3-Dipolar Cycloaddition Approach

被引:21
|
作者
Zhang, Zhe [1 ]
Giampa, Geoffrey M. [1 ]
Draghici, Cristian [1 ]
Huang, Qiufeng [1 ]
Brewer, Matthias [1 ]
机构
[1] Univ Vermont, Burlington, VT 05405 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
EQUIVALENTS; DIASTEREOISOMERS; GLYCOALKALOIDS;
D O I
10.1021/ol4004993
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.
引用
收藏
页码:2100 / 2103
页数:4
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