BETA-LACTAMS .3. ASYMMETRIC TOTAL SYNTHESIS OF NEW NONNATURAL 1-BETA-METHYLCARBAPENEMS EXHIBITING STRONG ANTIMICROBIAL ACTIVITIES AND STABILITY AGAINST HUMAN RENAL DEHYDROPEPTIDASE-I

被引：72

作者：

NAGAO, Y ^{[1
]}

NAGASE, Y ^{[1
]}

KUMAGAI, T ^{[1
]}

MATSUNAGA, H ^{[1
]}

ABE, T ^{[1
]}

SHIMADA, O ^{[1
]}

HAYASHI, T ^{[1
]}

INOUE, Y ^{[1
]}

机构：

[1] LEDERLE JAPAN LTD,CHEM & FORMULAT LABS,SHIKI,SAITAMA 353,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期

关键词：

D O I：

10.1021/jo00041a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5. Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d). Compounds 17a,b were successfully converted to new, non-natural 1-beta-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.

引用

页码：4243 / 4249

页数：7

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