First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers

被引：10

作者：

Claudel, S

Olszewski, TK

Mutzenardt, P

Aroulanda, C

Coutrot, P

Grison, C

机构：

[1] Lab Chim Biomol, UMR 5032, F-34296 Montpellier, France

[2] Univ Nancy 1, Lab Chim Organ Biomol, UMR 7565, F-54506 Vandoeuvre Les Nancy, France

[3] Univ Nancy 1, Lab Nethodol RMN, UMR 7565, F-54506 Vandoeuvre Les Nancy, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 08期

关键词：

potassium aeshynomate; vinylogous peptides; aminoaldehydes; Horner reaction; asymmetric dihydroxylation; natural product;

D O I：

10.1016/j.tet.2005.11.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting gamma-amino alpha, beta-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1787 / 1798

页数：12

共 18 条

[1] Total synthesis of AI-77-B: stereoselective hydroxylation of 4-alkenylazetidinones [J].