OLIVANIC ACID ANALOGS .6. BIOMIMETIC SYNTHESIS OF (+/-)-PS-5, (+/-)-6-EPI-PS-5, AND (+/-)-BENZYL MM22381

被引：8

作者：

BATESON, JH

HICKLING, RI

SMALE, TC

SOUTHGATE, R

机构：

[1] Beecham Pharmaceuticals, Research Division, Betchworth, Surrey RH3 7AJ, Brockham Park

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 06期

关键词：

D O I：

10.1039/p19900001793

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition of thiols to 6-substituted azabicyclo[3.2.0]hept-2-ene-2-carboxylates, followed by reintroduction of the double bond with iodobenzene dichloride-pyridine under anhydrous conditions, provides a biomimetic strategy for the synthesis of 3-alkylthio-substituted olivanic acids (carbapenems) and their derivatives. This is illustrated by syntheses of representatives of the PS-5 and MM22381 series of antibacterial natural products.

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页码：1793 / 1801

页数：9

相关论文

共 31 条

[11] BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].

CAINELLI, G ;

PANUNZIO, M ;

GIACOMINI, D ;

MARTELLI, G ;

SPUNTA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6879-6880

[12]

CORBETT DF, 1980, J CHEM SOC CHEM COMM, P1082

[13]

FUKAGAWA Y, 1985, SPEC PUBL R SOC CHEM, V52, P163

[14] CHELATION-CONTROLLED ENANTIOSELECTIVE SYNTHESIS OF KEY INTERMEDIATES FOR THE PREPARATION OF CARBAPENEM ANTIBIOTICS PS-5 AND 1-BETA-METHYL-PS-5 [J].

GENNARI, C ;

COZZI, PG .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4015-4021

[15] A NEW CARBAPENAM NO-17927 D-SUBSTANCE [J].

HANEISHI, T ;

NAKAJIMA, M ;

SERIZAWA, N ;

INUKAI, M ;

TAKIGUCHI, Y ;

ARAI, M ;

SATOH, S ;

KUWANO, H ;

TAMURA, C .

JOURNAL OF ANTIBIOTICS, 1983, 36 (11) :1581-1584

[16] THE SYNTHESIS OF THE 1-CARBAPENEM ANTIBIOTIC (+/-)-PS-5 AND ITS 6-EPI ANALOG [J].

HATANAKA, M ;

NITTA, H ;

ISHIMARU, T .

TETRAHEDRON LETTERS, 1984, 25 (22) :2387-2390

[17] STUDIES ON TERPENES .4. SYNTHESIS OF OPTICALLY-ACTIVE GRANDISOL, BOLL-WEEVIL PHEROMONE [J].

HOBBS, PD ;

MAGNUS, PD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (15) :4594-4600

[18] STEREOCHEMISTRY OF METHYLATION IN THIENAMYCIN BIOSYNTHESIS - EXAMPLE OF A METHYL TRANSFER FROM METHIONINE WITH RETENTION OF CONFIGURATION [J].

HOUCK, DR ;

KOBAYASHI, K ;

WILLIAMSON, JM ;

FLOSS, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5365-5366

[19] STUDIES ON THE BIOSYNTHESIS OF CARBAPENEM ANTIBIOTICS .4. BETA-ALANINE IN THE C-3 PANTETHEINYL SIDE-CHAIN OF THE OA-6129 GROUP OF CARBAPENEMS [J].

KUBO, K ;

ISHIKURA, T ;

FUKAGAWA, Y .

JOURNAL OF ANTIBIOTICS, 1985, 38 (07) :904-911

[20]

LUKAS HJ, 1955, ORG SYNTH COLL, V3, P482

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