NOVEL, STEREOSELECTIVE SYNTHESES OF PENEM ANTIBIOTICS - EFFICIENT, FORMAL SYNTHESES OF SCH 34343

被引：4

作者：

HOU, D ^{[1
]}

MAS, JL ^{[1
]}

CHAN, TM ^{[1
]}

WONG, YS ^{[1
]}

STEINMAN, M ^{[1
]}

MCPHAIL, AT ^{[1
]}

机构：

[1] DUKE UNIV,PAUL M GROSS CHEM LAB,DURHAM,NC 27708

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(01)80920-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Novel, stereoselective syntheses of (3S, 4R, 5R)-1-(allyloxycarbonyl)methyl-3-[1-hydroxyethyl]-4-beta-naphthoxy(thiocarbonyl)thio-2-azetidinone (13) and (3S, 4R, 5R, 3'S, 4'R, 5'R)-4,4'-dithio-bis-l-(allyloxy-carbonyl)methyl-3-[-1-hydroxyethyl]-2-azetidinone (22), key intermediates in the synthesis of the penem antibiotic Sch 34343, were developed starting from readily available 6-aminopenicillanic acid. Advantages of these routes include 1) the highly stereospecific introduction of the hydroxyethyl sidechain with the desired (R)-configuration and 2) the retention of the sulfur of the starting material.

引用

页码：2171 / 2176

页数：6

共 22 条

[1]

AIMETTI JA, 1979, TETRAHEDRON LETT, V20, P3805

[2] SILVER-ASSISTED 1,2-CLEAVAGE OF PENICILLINS - A 3-STEP SYNTHESIS OF OPTICALLY-ACTIVE PENEMS [J].