SYNTHESIS OF OPTICALLY-ACTIVE BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF IMINES WITH OPTICALLY-ACTIVE CHROMIUM CARBENE COMPLEXES .2. SYNTHESIS OF 1-CARBACEPHALOTHIN AND 3-ANA RELAYS

被引：49

作者：

NARUKAWA, Y

JUNEAU, KN

SNUSTAD, D

MILLER, DB

HEGEDUS, LS

机构：

[1] Department of Chemistry, Colorado State University, Colorado 80523, Fort Collins

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 20期

关键词：

D O I：

10.1021/jo00046a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A relay (3) to optically active 1-carbacephalothin (4) was prepared in modest yield with high stereoselectivity by the photochemical reaction of optically active chromium carbene complex 1 with functionalized imine 2. In contrast, the photochemical reaction of carbene complex 1 with imine precursors 15a,b to the nocardicins was much less stereoselective.

引用

收藏

页码：5453 / 5462

页数：10

相关论文

共 32 条

[1]

BODANSZKY M, 1984, PRACTICE PEPTIDE SYN, P19

[2] TRIFLUOROMETHANESULFONYL AZIDE - ITS REACTION WITH ALKYL AMINES TO FORM ALKYL AZIDES [J].

CAVENDER, CJ ;

SHINER, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3567-&

[3] A NOVEL SYNTHESIS OF (+/-)-3-AMINONOCARDICINIC ACID [J].

CHIBA, K ;

MORI, M ;

BAN, Y .

TETRAHEDRON, 1985, 41 (02) :387-392

[4]

CURRAN WV, 1982, ANTIBIOT, V35, P329

[5] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .1. APPLICATION OF CHIRAL OXAZOLIDONES IN THE STAUDINGER REACTION [J].

EVANS, DA ;

SJOGREN, EB .

TETRAHEDRON LETTERS, 1985, 26 (32) :3783-3786

[6] TOTAL SYNTHESES OF (+/-)-1-CARBACEFOXITIN AND (+/-)-1-CARBA CEFAMANDOLE AND (+/-)-1-OXACEFAMANDOLE [J].

FIRESTONE, RA ;

FAHEY, JL ;

MACIEJEWICZ, NS ;

PATEL, GS ;

CHRISTENSEN, BG .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (04) :551-556

[7] TOTAL SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .8. STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-1-CARBACEPHALOTHIN [J].

GUTHIKONDA, RN ;

CAMA, LD ;

CHRISTENSEN, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (24) :7584-7585

[8] NOCARDICIN-A, A NEW MONOCYCLIC BETA-LACTAM ANTIBIOTIC .2. STRUCTURE DETERMINATION OF NOCARDICIN-A AND NOCARDICIN-B [J].

HASHIMOTO, M ;

KOMORI, T ;

KAMIYA, T .

JOURNAL OF ANTIBIOTICS, 1976, 29 (09) :890-901

[9] NOCARDICIN A AND B, NOVEL MONOCYCLIC BETA-LACTAM ANTIBIOTICS FROM A NOCARDIA SPECIES [J].

HASHIMOTO, M ;

KOMORI, T ;

KAMIYA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :3023-3025

[10] SYNTHESIS OF MONOCYCLIC BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF CHROMIUM CARBENE COMPLEXES WITH S-1,3,5-TRIAZINES [J].

HEGEDUS, LS ;

DANDREA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :3113-3116

← 1 2 3 4 →