Asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB

被引：58

作者：

DeMong, DE ^{[1
]}

Williams, RM ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 28期

关键词：

D O I：

10.1021/ja0351241

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin 113 has been accomplished. The synthesis features the use of an enolate-aldimine condensation between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means of preparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangement was exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.

引用

页码：8561 / 8565

页数：5

共 50 条

[1] Asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB
[J]. Williams, R.M. (rmw@lamar.colostate.edu), 1600, American Chemical Society (125):
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