Stereoselective Synthesis of the Epicoccin Core

被引：23
|
作者：
Gross, Ulrike [1 ]
Nieger, Martin [2 ]
Braese, Stefan [1 ]
机构：
[1] Karlsruhe Inst Technol, Inst Organ Chem, Karlsruhe, Germany
[2] Univ Helsinki, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 20期
关键词：
ONE-POT SYNTHESIS; UNPROTECTED AMINO-ACIDS; GLIOTOXIN; ANALOGS;
D O I：
10.1021/ol901919c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short, convergent, and asymmetric synthesis of the epicoccin core was achieved using a phosphite-promoted one-step condensation of a complex proline-type amino acid. Key features of the assembly of this amino acid were a double-bond isomerization/vinylation/ring-closing metathesis strategy as well as an efficient, highly diastereoselective [2 + 2] cycloaddition of a ketene to an enecarbamate, derived from L-pyroglutamic acid.
引用
收藏
页码：4740 / 4742
页数：3
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