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

页码：4740 / 4742

页数：3

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