Total Synthesis of (±)-Calcaridine A and (±)-epi-Calcaridine A

被引:28
|
作者
Koswatta, Panduka B. [1 ]
Sivappa, Rasapalli [1 ]
Dias, H. V. Rasika [1 ]
Lovely, Carl J. [1 ]
机构
[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA
关键词
D O I
10.1021/ol802018r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the Leucetta alkaloid calcaridine A is described based on a biosynthetic postulate. Application of an oxidative rearrangement of a 4,5-disubstituted imidazole leads to the formation of both calcaridine A and epi-calcaridine A. An X-ray crystal structure determination on the latter has allowed the assignment of the relative configuration of the epimeric natural product and calcaridine A by extrapolation.
引用
收藏
页码:5055 / 5058
页数:4
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