A practical synthesis of a key intermediate for the production of β-lactam antibiotics.

被引：23

作者：

Cainelli, G ^{[1
]}

Galletti, P ^{[1
]}

Giacomini, D ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(98)01700-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(p-methoxyphenyl)-hexahydro-1,3,5-triazine in presence of a Lewis acid and (R)-3-(t-butyldimethylsilyloxy)butyric acid chloride with Et3N directly furnish (3S,1'R)-N-p-methoxyphenyl-3- (1-t-butyldimethylsilyloxy)ethylazetidin-2-one with good diastereoselectivity. This product is transformed into the 4-acetoxy-azetidinone 1, a key intermediate in the synthesis of beta-lactam antibiotics. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7779 / 7782

页数：4

共 17 条

[1] CHEMOENZYMATIC PREPARATION OF A KEY INTERMEDIATE FOR CARBAPENEM SYNTHESIS STARTING FROM ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-ASTERISK) [J].

BANFI, L ;

GUANTI, G ;

NARISANO, E .

TETRAHEDRON, 1993, 49 (33) :7385-7392

[2] Penicillin G acylase mediated synthesis of the enantiopure(S)-3-amino-azetidin-2-one [J].

Cainelli, G ;

Giacomini, D ;

Galletti, P ;

DaCol, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3231-3235

[3] A SEMIEMPIRICAL THEORETICAL-STUDY ON THE FORMATION OF BETA-LACTAMS FROM KETENES AND IMINES [J].

COSSIO, FP ;

UGALDE, JM ;

LOPEZ, X ;

LECEA, B ;

PALOMO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :995-1004

[4] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .4. A FORMAL SYNTHESIS OF THIENAMYCIN [J].

EVANS, DA ;

SJOGREN, EB .

TETRAHEDRON LETTERS, 1986, 27 (41) :4961-4964

[5] A CONTRIBUTION TO THE CONFUSION SURROUNDING THE REACTION OF KETENES WITH IMINES TO PRODUCE BETA-LACTAMS - A COMPARISON OF STEREOSELECTIVITY DEPENDENCE ON THE METHOD OF KETENE GENERATION - ACID CHLORIDE TRIETHYLAMINE VS PHOTOLYSIS OF CHROMIUM CARBENE COMPLEXES [J].

HEGEDUS, LS ;

MONTGOMERY, J ;

NARUKAWA, Y ;

SNUSTAD, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5784-5791

[6] 3-ACYLTETRAMIC ACID ANTIBIOTICS .3. AN APPROACH TO THE SYNTHESIS OF BU-2313 [J].

IRELAND, RE ;

WARDLE, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1780-1789

[7] TOTAL SYNTHESIS OF MONOCYCLIC BETA-LACTAM ANTIBIOTICS, NOCARDICIN-A AND NOCARDICIN-D [J].

KAMIYA, T ;

HASHIMOTO, M ;

NAKAGUCHI, O ;

OKU, T .

TETRAHEDRON, 1979, 35 (03) :323-328

[8]

LOPEZ R, 1993, J ORG CHEM, V58, P7037

[9]

MICKEL S, 1985, ALDRICHIM ACTA, V18, P95

[10] RUTHENIUM-CATALYZED OXIDATION OF BETA-LACTAMS WITH MOLECULAR-OXYGEN AND ALDEHYDES [J].

MURAHASHI, SI ;

SAITO, T ;

NAOTA, T ;

KUMOBAYASHI, H ;

AKUTAGAWA, S .

TETRAHEDRON LETTERS, 1991, 32 (42) :5991-5994

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