Successive copper(I)-catalyzed cross-couplings in one pot: A novel and efficient starting point for synthesis of carbapenems

被引：53

作者：

Jiang, Biao ^{[1
]}

Tian, Hua ^{[1
]}

Huang, Zuo-Gang ^{[1
]}

Xu, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 13期

关键词：

D O I：

10.1021/ol800845r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient approach for synthesizing a series of 2-sulfide carbapenems has been developed using two successive Cu(I)-catalyzed cross-couplings in a single pot. The method involves highly selective intramolecular coupling of lactam and dihaloalkene using 2,2'-bipyridine as a ligand, followed by intermolecular C-S formation in the presence of another ligand (1,10-phenanthroline, PPh3) and mercaptan.

引用

页码：2737 / 2740

页数：4

共 45 条

[1] STRUCTURE AND ABSOLUTE-CONFIGURATION OF THIENAMYCIN [J].

ALBERSSCHONBERG, G ;

ARISON, BH ;

HENSENS, OD ;

HIRSHFIELD, J ;

HOOGSTEEN, K ;

KACZKA, EA ;

RHODES, RE ;

KAHAN, JS ;

KAHAN, FM ;

RATCLIFFE, RW ;

WALTON, E ;

RUSWINKLE, LJ ;

MORIN, RB ;

CHRISTENSEN, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) :6491-6499

[2] THE USE OF RADICAL CYCLIZATION IN THE PREPARATION OF SUBSTITUTED METHYL CARBAPENEM ANTIBIOTIC PRECURSORS [J].

ANAYA, J ;

BARTON, DHR ;

GERO, SD ;

GRANDE, M ;

MARTIN, N ;

TACHDIJIAN, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (06) :867-869

[3] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[4] SYNTHESIS OF OLIVANIC ACID ANALOGS - A FACILE ROUTE TO 3-(2-PYRIMIDINYLTHIO-) SUBSTITUTED DERIVATIVES [J].

BAXTER, AJG ;

DAVIS, P ;

PONSFORD, RJ ;

SOUTHGATE, R .

TETRAHEDRON LETTERS, 1980, 21 (52) :5071-5074

[5] Reaction of alkynes with iodine monochloride revisited [J].

Bellina, F ;

Colzi, F ;

Mannina, L ;

Rossi, R ;

Viel, S .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10175-10177

[6] TOTAL SYNTHESIS OF THIENAMYCIN ANALOGS .1. SYNTHESIS OF THIENAMYCIN NUCLEUS AND DL-DESCYSTEAMINYLTHIENAMYCIN [J].

CAMA, LD ;

CHRISTENSEN, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (25) :8006-8007

[7] Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950 [J].

Coleman, RS ;

Liu, PH .

ORGANIC LETTERS, 2004, 6 (04) :577-580

[8] Regulation and biosynthesis of carbapenem antibiotics in bacteria [J].

Coulthurst, SJ ;

Barnard, AML ;

Salmond, GPC .

NATURE REVIEWS MICROBIOLOGY, 2005, 3 (04) :295-306

[9] Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions [J].

Dehli, JR ;

Legros, J ;

Bolm, C .

CHEMICAL COMMUNICATIONS, 2005, (08) :973-986

[10] Preference of 4-exo ring closure in copper-catalyzed intramolecular coupling of vinyl bromides with alcohols [J].

Fang, Yewen ;

Li, Chaozhong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) :8092-+

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