Preparation of β-amino-α-mercapto acids and amides:: stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

被引：18

作者：

Lee, SH

Qi, X

Yoon, JY

Nakamura, K

Lee, YS

机构：

[1] Seoul Natl Univ, Coll Engn, Sch Chem Engn, Kwanak Gu, Seoul 151742, South Korea

[2] Dalian Univ Technol, Sch Chem Engn, Dalian 116012, Peoples R China

[3] Silla Univ, Dept New Mat Chem, Pusan 617736, South Korea

[4] Silla Univ, Biofunct Mat Res Ctr, Pusan 617736, South Korea

[5] Inst Med Mol Design, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 14期

关键词：

3-amino-2-mercapto acid; oxazoline; taxol; sharpless asymmetric aminohydroxylation;

D O I：

10.1016/S0040-4020(02)00175-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2777 / 2787

页数：11

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