DIRECT CONVERSION OF N-ALKOXY BETA-LACTAMS TO CARBAPENAMS - APPLICATION TO THE SYNTHESIS OF THE BICYCLIC PS-5 KETO ESTER

被引：24

作者：

WILLIAMS, MA ^{[1
]}

HSIAO, CN ^{[1
]}

MILLER, MJ ^{[1
]}

机构：

[1] UNIV NOTRE DAME,DEPT CHEM & BIOCHEM,NOTRE DAME,IN 46556

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 08期

关键词：

D O I：

10.1021/jo00008a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and direct conversion of N-alkoxy beta-lactams to the carbapenam ring system is described. This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement. The title reaction is applied to the construction of the methyl ester of the bicyclic beta-lactam precursor of PS-5.

引用

页码：2688 / 2694

页数：7

共 45 条

[41] A SYNTHESIS OF ANTIBIOTIC (+/-)-PS-5
WASSERMAN, HH
HAN, WT
[J]. TETRAHEDRON LETTERS, 1984, 25 (34) : 3747 - 3750
[42] SYNTHESIS OF THE CARBAPENAM RING-SYSTEM VIA CARBENE MEDIATED REARRANGEMENT OF AN N-BENZYLOXY-BETA-LACTAM
WILLIAMS, MA
MILLER, MJ
[J]. TETRAHEDRON LETTERS, 1990, 31 (13) : 1807 - 1810
[43] HEMIKETAL FORMATION AND SUBSEQUENT INTRAMOLECULAR ACYLATION OF AN N-HYDROXY BETA-LACTAM
WILLIAMS, MA
MILLER, MJ
RATH, NP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 1293 - 1296
[44] HETEROATOM ACTIVATED BETA-LACTAM ANTIBIOTICS - SYNTHESIS OF BIOLOGICALLY-ACTIVE SUBSTITUTED N-OXY-3-AMINO-2-AZETIDINONES (OXAMAZINS)
WOULFE, SR
MILLER, MJ
[J]. TETRAHEDRON LETTERS, 1984, 25 (31) : 3293 - 3296
[45] STRUCTURE AND STEREOCHEMISTRY OF ANTIBIOTIC PS-5
YAMAMOTO, K
YOSHIOKA, T
KATO, Y
SHIBAMOTO, N
OKAMURA, K
SHIMAUCHI, Y
ISHIKURA, T
[J]. JOURNAL OF ANTIBIOTICS, 1980, 33 (08) : 796 - 803

← 1 2 3 4 5 →