Convenient syntheses of (3S,5S)-carbapenam-3-carboxylates and their biosynthetic relevance

被引：18

作者：

Bycroft, BW ^{[1
]}

Chhabra, SR ^{[1
]}

Kellam, B ^{[1
]}

Smith, P ^{[1
]}

机构：

[1] Univ Nottingham, Sch Pharmaceut Sci, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 05期

关键词：

carbapenam-3-carboxylate; biosynthesis; absolute configuration; beta-lactam; tris(1,3-dihydro-2-benzoxazolin-3-yl)phosphine; oxide;

D O I：

10.1016/S0040-4039(02)02731-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from readily available glutamate derivatives, facile stereoselective syntheses of (3S,5S)-carbapenam-3-carboxylates have been developed. Their significance in confirming the absolute configuration of the natural material is discussed. (C) 2003 Published by Elsevier Science Ltd.

引用

页码：973 / 976

页数：4

共 15 条

[1]

BUCHI MD, 1983, J ORG CHEM, V48, P1439

[2] THE ISOLATION AND CHARACTERIZATION OF (3R,5R)-CARBAPENAM-3-CARBOXYLIC AND (3S,5R)-CARBAPENAM-3-CARBOXYLIC ACID FROM SERRATIA AND ERWINIA SPECIES AND THEIR PUTATIVE BIOSYNTHETIC ROLE [J].

BYCROFT, BW ;

MASLEN, C ;

BOX, SJ ;

BROWN, AG ;

TYLER, JW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1623-1625

[3] A CHIRAL SYNTHESIS OF TRANS-CARBAPENAM-3-CARBOXYLIC ACID AND THE ASSIGNMENT OF (3S,5S) CONFIGURATION TO THE CORRESPONDING PRODUCT FROM SERRATIA AND ERWINIA SPECIES [J].

BYCROFT, BW ;

CHHABRA, SR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :423-425

[4] THE BIOSYNTHETIC IMPLICATIONS OF ACETATE AND GLUTAMATE INCORPORATION INTO (3R,5R)-CARBAPENAM-3-CARBOXYLIC ACID AND (5R)-CARBAPEN-2-EM-3-CARBOXYLIC ACID BY SERRATIA SP [J].

BYCROFT, BW ;

MASLEN, C ;

BOX, SJ ;

BROWN, A ;

TYLER, JW .

JOURNAL OF ANTIBIOTICS, 1988, 41 (09) :1231-1242

[5] Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole [J].

Gilchrist, TL ;

Lemos, A ;

Ottaway, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (20) :3005-3012

[6] Three unusual reactions mediate carbapenem and carbapenam biosynthesis [J].

Li, RF ;

Stapon, A ;

Blanchfield, JT ;

Townsend, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9296-9297

[7] Analysis of bacterial carbapenem antibiotic production genes reveals a novel beta-lactam biosynthesis pathway [J].

McGowan, SJ ;

Sebaihia, M ;

Porter, LE ;

Stewart, GSAB ;

Williams, P ;

Bycroft, BW ;

Salmond, GPC .

MOLECULAR MICROBIOLOGY, 1996, 22 (03) :415-426

[8] Analysis of the carbapenem gene cluster of Erwinia carotovora: definition of the antibiotic biosynthetic genes and evidence for a novel beta-lactam resistance mechanism [J].

McGowan, SJ ;

Sebaihia, M ;

OLeary, S ;

Hardie, KR ;

Williams, P ;

Stewart, GSAB ;

Bycroft, BW ;

Salmond, GPC .

MOLECULAR MICROBIOLOGY, 1997, 26 (03) :545-556

[9] Bacterial production of carbapenems and clavams:: evolution of β-lactam antibiotic pathways [J].

McGowan, SJ ;

Bycroft, BW ;

Salmond, GPC .

TRENDS IN MICROBIOLOGY, 1998, 6 (05) :203-208

[10] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE PARA-NITROBENZYL ESTER OF SQ27860 [J].

MIYASHITA, M ;

CHIDA, N ;

YOSHIKOSHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) :195-196

← 1 2 →