NOVEL ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS WITH 3-(1'-HYDROXYETHYL) SUBSTITUENTS - BORON REAGENT MEDIATED ALDOL REACTION OF CHIRAL IMINES AND SILYL KETENE ACETALS DERIVED FROM 3-HYDROXYBUTYRATE

被引：7

作者：

HATTORI, K ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,DEPT APPL CHEM,NAGOYA 46401,JAPAN

来源：

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

关键词：

D O I：

10.1016/S0960-894X(01)80951-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An asymmetric reaction of chiral imines with silyl ketene acetals, prepared from (3R)-hydroxybutyrate, mediated by a boron reagent is described. The method succesSfullY affords beta-amino esters with high diastereoselectivity, which can be converted to optically pure beta-lactams. This result indicated that a formal total synthesis of (+)-thienamycin is achieved by a simple and practical procedure.

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页码：2337 / 2342

页数：6

相关论文

共 22 条

[11]

HATTORI K, 1993, SYNLETT, P239

[12] STEREOCONTROLLED SYNTHESIS OF (+)-THIENAMYCIN FROM 3(R)-HYDROXYBUTYRIC ACID [J].

IIMORI, T ;

SHIBASAKI, M .

TETRAHEDRON LETTERS, 1985, 26 (12) :1523-1526

[13] NOVEL SYNTHESES OF THE CARBAPENEM KEY INTERMEDIATES, (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE AND (3S,4R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-CARBOXYMETHYL-2-AZETIDINONE, FROM (S)-ETHYL LACTATE [J].

ITO, Y ;

KOBAYASHI, Y ;

KAWABATA, T ;

TAKASE, M ;

TERASHIMA, S .

TETRAHEDRON, 1989, 45 (18) :5767-5790

[14]

KLEINNMAN EF, 1991, COMPREHENSIVE ORGANI, V2

[15] FURTHER-STUDIES ON THE ACETONEDICARBOXYLATE ROUTE TO THIENAMYCIN - STEREOCHEMICAL INVERSION AT THE LACTONE STAGE [J].

MELILLO, DG ;

LIU, T ;

RYAN, K ;

SLETZINGER, M ;

SHINKAI, I .

TETRAHEDRON LETTERS, 1981, 22 (10) :913-916

[16] A PRACTICAL SYNTHESIS OF (+/-)-THIENAMYCIN [J].

MELILLO, DG ;

SHINKAI, I ;

LIU, T ;

RYAN, K ;

SLETZINGER, M .

TETRAHEDRON LETTERS, 1980, 21 (29) :2783-2786

[17] COMPLETE STEREOSELECTIVE SYNTHESIS OF CHIRAL INTERMEDIATES FOR THIENAMYCIN AND RELATED ANTIBIOTICS [J].

OGUNI, N ;

OHKAWA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (20) :1376-1377

[18] THE SYNTHESIS OF 3-(1'-HYDROXYETHYL)-2-AZETIDINONE-4-YL ACETIC-ACID VIA DIANION CHEMISTRY - AN IMPORTANT INTERMEDIATE IN THIENAMYCIN TOTAL SYNTHESIS [J].

SHINKAI, I ;

LIU, T ;

REAMER, RA ;

SLETZINGER, M .

TETRAHEDRON LETTERS, 1982, 23 (47) :4899-4902

[19] A NOVEL, DOUBLE-ASYMMETRIC ALDOL APPROACH TO THE SYNTHESIS OF A 1-BETA-METHYL CARBAPENEM ANTIBIOTIC PRECURSOR [J].

SHIRAI, F ;

NAKAI, T .

TETRAHEDRON LETTERS, 1988, 29 (49) :6461-6464

[20]

SIOZAKI M, 1981, TETRAHEDRON LETT, V22, P5205