A practical and efficient preparation of the releasable naphthosultam side chain of a novel anti-MRSA carbapenem

被引：35

作者：

Miller, RA ^{[1
]}

Humphrey, GR ^{[1
]}

Lieberman, DR ^{[1
]}

Ceglia, SS ^{[1
]}

Kennedy, DJ ^{[1
]}

Grabowski, EJJ ^{[1
]}

Reider, PJ ^{[1
]}

机构：

[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 05期

关键词：

D O I：

10.1021/jo991490k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical large-scale synthesis of the naphthosultam-based side chain of the anti-MRSA antibiotic 1 has been achieved in 29% overall yield over seven steps from l-methylnaphthalene. The synthesis was completed without the use of protecting groups, featuring a novel naphthosultam annelation, a chemoselective acid-catalyzed triflation, and the use of a novel naphthosultam dianion to effect functionalization through benzylic metalation.

引用

页码：1399 / 1406

页数：8

共 29 条

[1] KINETIC SULFUR ISOTOPE EFFECTS IN AROMATIC BROMODESULFONATION [J].