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

相关论文

共 44 条

[1]

Akasaka K, 1999, CHEM PHARM BULL, V47, P1525

[2]

Akasaka K, 1999, CHEM PHARM BULL, V47, P1532

[3] A novel series of matrix metalloproteinase inhibitors for the treatment of inflammatory disorders [J].

Baxter, AD ;

Bird, J ;

Bhogal, R ;

Massil, T ;

Minton, KJ ;

Montana, J ;

Owen, DA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (07) :897-902

[4] Mercaptoacyl matrix metalloproteinase inhibitors: The effect of substitution at the mercaptoacyl moiety [J].

Baxter, AD ;

Bhogal, R ;

Bird, JB ;

Buckley, GM ;

Gregory, DS ;

Hedger, PC ;

Manallack, DT ;

Massil, T ;

Minton, KJ ;

Montana, JG ;

Neidle, S ;

Owen, DA ;

Watson, RJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (21) :2765-2770

[5] 2,4-Dinitrophenyl 4-methoxybenzyl disulfide: A new efficient reagent for the electrophilic sulfenylation of beta-amino ester enolates [J].

Bischoff, L ;

David, C ;

Martin, L ;

Meudal, H ;

Roques, BP ;

FournieZaluski, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4848-4850

[6] N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].

Bruncko, M ;

Schlingloff, G ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486

[7] Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines - The asymmetric synthesis of alpha,alpha-disubstituted amino acids [J].

Burgaud, BGM ;

Horwell, DC ;

Padova, A ;

Pritchard, MC .

TETRAHEDRON, 1996, 52 (40) :13035-13050

[8] DIFFERENTIAL INHIBITION OF AMINOPEPTIDASE-A AND AMINOPEPTIDASE-N BY NEW BETA-AMINO THIOLS [J].

CHAUVEL, EN ;

LLORENSCORTES, C ;

CORIC, P ;

WILK, S ;

ROQUES, BP ;

FOURNIEZALUSKI, MC .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (18) :2950-2957

[9] Optimal recognition of neutral endopeptidase and angiotensin-converting enzyme active sites by mercaptoacyldipeptides as a means to design potent dual inhibitors [J].

Coric, P ;

Turcaud, S ;

Meudal, H ;

Roques, BP ;

FournieZaluski, MC .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (06) :1210-1219

[10] PhI=NSes: A new iminoiodinane reagent for the copper-catalyzed aziridination of olefins [J].

Dauban, P ;

Dodd, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5304-5307

← 1 2 3 4 5 →