Diastereoselective synthesis of a key intermediate for the preparation of tricyclic β-lactam antibiotics

被引：33

作者：

Matsumoto, T ^{[1
]}

Murayama, T ^{[1
]}

Mitsuhashi, S ^{[1
]}

Miura, T ^{[1
]}

机构：

[1] Takasago Int Corp, Cent Res Lab, Hiratsuka, Kanagawa 2540073, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

carbapenems; asymmetric synthesis; hydrogenation; aldol reactions;

D O I：

10.1016/S0040-4039(99)00929-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of (S)-5 has been accomplished with an excellent enantiomeric hydrogenation of racemic 5 using ruthenium-BINAP-diamine-KOH system, followed by oxidation. Magnesium enolate of (2S)-2-methoxycyclohexanone [(S)-5] reacts with the 4-acetoxyazetidinone 4 to give the key intermediate 3 viith high yield and diastereoselectivity for the synthesis of sanfetrinem 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5043 / 5046

页数：4

共 10 条

[1] Synthesis and antibacterial activity of 4- and 8-methoxy trinems [J].

Andreotti, D ;

Rossi, T ;

Gaviraghi, G ;

Donati, D ;

Marchioro, C ;

DiModugno, E ;

Perboni, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (04) :491-496

[2] THE SYNTHESIS OF A KEY INTERMEDIATE OF TRICYCLIC BETA-LACTAM ANTIBIOTICS [J].

BISMARA, C ;

DIFABIO, R ;

DONATI, D ;

ROSSI, T ;

THOMAS, RJ .

TETRAHEDRON LETTERS, 1995, 36 (24) :4283-4286

[3] IN-VITRO ACTIVITY OF THE TRIBACTAM GV104326 AGAINST GRAM-POSITIVE, GRAM-NEGATIVE, AND ANAEROBIC-BACTERIA [J].

DIMODUGNO, E ;

ERBETTI, I ;

FERRARI, L ;

GALASSI, G ;

HAMMOND, SM ;

XERRI, L .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1994, 38 (10) :2362-2368

[4] The stereoselective synthesis of a key intermediate of the trinem antibiotic Sanfetrinem [J].

Ghiron, C ;

Piga, E ;

Rossi, T ;

Tamburini, B ;

Thomas, RJ .

TETRAHEDRON LETTERS, 1996, 37 (22) :3891-3894

[5] A highly stereoselective and practical total synthesis of the tricyclic beta-lactam antibiotic GV104326 (4-methoxytrinem) [J].

Hanessian, S ;

Rozema, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) :9884-9891

[6] The use of zinc enolates in the synthesis of a key intermediate for the preparation of trinem antibiotics. [J].

Kennedy, G ;

Rossi, T ;

Tamburini, B .

TETRAHEDRON LETTERS, 1996, 37 (41) :7441-7444

[7] CATIONIC BINAP-RU(II) HALIDE-COMPLEXES - HIGHLY EFFICIENT CATALYSTS FOR STEREOSELECTIVE ASYMMETRIC HYDROGENATION OF ALPHA-FUNCTIONALIZED AND BETA-FUNCTIONALIZED KETONES [J].

MASHIMA, K ;

KUSANO, KH ;

SATO, N ;

MATSUMURA, Y ;

NOZAKI, K ;

KUMOBAYASHI, H ;

SAYO, N ;

HORI, Y ;

ISHIZAKI, T ;

AKUTAGAWA, S ;

TAKAYA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3064-3076

[8] Stereoselective hydrogenation of simple ketones catalyzed by Ruthenium(II) complexes [J].

Ohkuma, T ;

Ooka, H ;

Yamakawa, M ;

Ikariya, T ;

Noyori, R .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4872-4873

[9] Stereoselective synthesis of a key intermediate of sanfetrinem by means of a chelated tin(IV) enolate [J].

Rossi, T ;

Marchioro, C ;

Paio, A ;

Thomas, RJ ;

Zarantonello, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1653-1661

[10] Efficient procedures for the large-scale preparation of (1S,2S)-trans-2-methoxycyclohexanol, a key chiral intermediate in the synthesis of tricyclic beta-lactam antibiotics [J].

Stead, P ;

Marley, H ;

Mahmoudian, M ;

Webb, G ;

Noble, D ;

Ip, YT ;

Piga, E ;

Rossi, T ;

Roberts, S ;

Dawson, MJ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2247-2250

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