STUDIES ON LACTAMS .84. BETA-LACTAMS VIA ALPHA,BETA-UNSATURATED ACID-CHLORIDES - INTERMEDIATES FOR CARBAPENEM ANTIBIOTICS
Stereocontrolled synthesis of .alpha.-vinyl .beta.-lactams and their transformation to convenient intermediates for PS-5, PS-6, asparenomycin, and thienamycin are described.
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Published in | Journal of organic chemistry Vol. 55; no. 2; pp. 575 - 580 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
Amer Chemical Soc
19.01.1990
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Abstract | Stereocontrolled synthesis of .alpha.-vinyl .beta.-lactams and their transformation to convenient intermediates for PS-5, PS-6, asparenomycin, and thienamycin are described. |
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AbstractList | Stereocontrolled synthesis of .alpha.-vinyl .beta.-lactams and their transformation to convenient intermediates for PS-5, PS-6, asparenomycin, and thienamycin are described. |
Author | BOSE, AK GHOSH, M MANHAS, MS |
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References | KRONENTHAL, DR (WOS:A1982NV96100016) 1982; 47 HASHIMOTO, T (WOS:A1980KQ61400018) 1980; 28 MARTEL, A (WOS:A1983QK73100037) 1983; 61 FETTER, J (WOS:A1986D727400019) 1986 BOUFFARD FA (WOS:A1990CJ67400035.4) 1980; 45 SATO, M (WOS:A1987K229300009) 1987; 26 EDWARDS, JA (WOS:A1974T058800026) 1974 GEORG, GI (WOS:A1985ASP3300046) 1985 MORIN RB (WOS:A1990CJ67400035.33) 1982; 2 KOPPEL GA (WOS:A1990CJ67400035.28) 1983 YOSHIDA, A (WOS:A1981MR09100023) 1981; 29 HART, DJ (WOS:A1986E058400072) 1986; 108 BUYNAK, JD (WOS:A1985ASG1400010) 1985; 26 ZAMBONI, R (WOS:A1979HK46800008) 1979; 57 BACHI, MD (WOS:A1980KL56200032) 1980 VANDERHAEGHE, H (WOS:A1975W316300009) 1975; 18 GEORG, GI (WOS:A1984TG45900001) 1984; 25 PFAENDLER, HR (WOS:A1980JJ63500045) 1980; 102 VEEN JMV (WOS:A1990CJ67400035.38) 1989; 54 FIRESTON.RA (WOS:A1974U696900017) 1974; 39 MANHAS MS (WOS:A1990CJ67400035.30) 1971 MANHAS, MS (WOS:A1986F279600003) 1986; 25 COSSIO, FP (WOS:A1989T219600004) 1989 GEORG, GI (WOS:A1988M076300041) 1988; 53 ODRIOZOLA, JM (WOS:A1988P085300032) 1988 KAMETANI T (WOS:A1990CJ67400035.26) 1982; 17 GEORG GI (WOS:A1990CJ67400035.15); 2 KAMETANI, T (WOS:A1980KV33700011) 1980; 14 HOLDEN KG (WOS:A1990CJ67400035.24) 1982; 2 GEORG, GI (WOS:A1987G075700023) 1987; 109 BUYNAK, JD (WOS:A1987H492600020) 1987 FETTER, J (WOS:A1985A122700004) 1985 BOSE, AK (WOS:A1986F128200013) 1986; 27 HART, DJ (WOS:A1985ATW8500003) 1985; 26 BUYNAK, JD (WOS:A1986C268000036) 1986; 51 KAMIYA, T (WOS:A1978GB23800017) 1978 HA, DC (WOS:A1987G536200009) 1987; 40 BOSE, AK (WOS:A1971K013400008) 1971 FETTER, J (WOS:A1986A151000006) 1986 BUYNAK, JD (WOS:A1985ATL7700012) 1985; 50 |
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SYNTHESIS OF THE (+/-)-DINORPENICILLIN-SPIROCYCLOPENTANE SYSTEM publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: BACHI, MD – start-page: 74 year: 1989 ident: WOS:A1989T219600004 article-title: THE ALPHA-BROMOESTER-IMINE CONDENSATION PROMOTED BY ZINC-TRIMETHYLCHLOROSILANE - A STEREOSPECIFIC SHORT FORMAL SYNTHESIS OF (+/-)-CARBAPENEM ANTIBIOTICS AND RELATED-COMPOUNDS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: COSSIO, FP – volume: 54 start-page: 5758 year: 1989 ident: WOS:A1990CJ67400035.38 publication-title: J ORG CHEM contributor: fullname: VEEN JMV – start-page: 3167 year: 1971 ident: WOS:A1971K013400008 article-title: STUDIES ON LACTAMS .16. STEREOCHEMISTRY OF BETA-LACTAM FORMATION publication-title: TETRAHEDRON LETTERS contributor: fullname: BOSE, AK – start-page: 1433 year: 1985 ident: WOS:A1985ASP3300046 article-title: STEREO-CONTROLLED AND ENANTIO-CONTROLLED SYNTHESIS OF CHIRAL INTERMEDIATES FOR THE TOTAL SYNTHESIS OF THIENAMYCIN AND RELATED BETA-LACTAM ANTIBIOTICS FROM 3-HYDROXYBUTYRATES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: GEORG, GI – volume: 29 start-page: 2899 year: 1981 ident: WOS:A1981MR09100023 article-title: 2-(ALKYLTHIO)PENEM-3-CARBOXYLIC ACIDS .4. SYNTHESIS OF (HYDROXYETHYL)-AZETIDINONE PRECURSORS TO 1-THIA ANALOGS OF THIENAMYCIN publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: YOSHIDA, A – start-page: 1453 year: 1986 ident: WOS:A1986D727400019 article-title: SIMPLE AND CONDENSED BETA-LACTAMS .7. SIDE-CHAIN EXTENSIONS OF SOME AZETIDIN-2-ONE DERIVATIVES, AND THE FORMATION OF MELILLOS LACTONE, A STRATEGIC INTERMEDIATE IN THE TOTAL SYNTHESIS OF THIENAMYCIN, FROM 3-ACETYL-1-BENZYL-4-CYANOMETHYLAZETIDIN-2-ONE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: FETTER, J – volume: 45 start-page: 130 year: 1980 ident: WOS:A1990CJ67400035.4 publication-title: J ORG CHEM contributor: fullname: BOUFFARD FA – volume: 108 start-page: 6054 year: 1986 ident: WOS:A1986E058400072 article-title: ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND THE CARBAPENEM ANTIBIOTIC (+)-PS-5 publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: HART, DJ – volume: 57 start-page: 1945 year: 1979 ident: WOS:A1979HK46800008 article-title: BETA-LACTAMS .7. SYNTHESIS OF 3-VINYL AND 3-ISOPROPENYL 4-SUBSTITUTED AZETIDINONES publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: ZAMBONI, R – volume: 2 year: 1982 ident: WOS:A1990CJ67400035.33 publication-title: CHEM BIOL BETA LACTA contributor: fullname: MORIN RB – start-page: 735 year: 1987 ident: WOS:A1987H492600020 article-title: THE PREPARATION OF THE 1ST ALPHA-VINYLIDENE-BETA-LACTAMS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: BUYNAK, JD – start-page: 248 year: 1983 ident: WOS:A1990CJ67400035.28 publication-title: SMALL RING HETEROC 2 contributor: fullname: KOPPEL GA – volume: 61 start-page: 613 year: 1983 ident: WOS:A1983QK73100037 article-title: NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .16. ALDOL CONDENSATIONS OF N-PROTECTED 4-TRITYLTHIO-2-AZETIDINONES publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: MARTEL, A – volume: 28 start-page: 2980 year: 1980 ident: WOS:A1980KQ61400018 article-title: SYNTHESIS OF AMINO-ACID AND 4,5-DIHYDRO-6H-1,3-THIAZINE DERIVATIVES FOR THE PREPARATION OF CEPHALOSPORIN COMPOUNDS publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: HASHIMOTO, T – volume: 2 ident: WOS:A1990CJ67400035.15 publication-title: IN PRESS SYNTHESIS T contributor: fullname: GEORG GI – volume: 14 start-page: 1967 year: 1980 ident: WOS:A1980KV33700011 article-title: FACILE SYNTHESIS OF CARBAPENEM ANTIBIOTICS - THE 1ST AND SIMPLE STEREOSELECTIVE SYNTHESIS OF ANTIBIOTIC PS-5 BENZYL ESTER publication-title: HETEROCYCLES contributor: fullname: KAMETANI, T – volume: 51 start-page: 1571 year: 1986 ident: WOS:A1986C268000036 article-title: ALPHA-ALKYLIDENE BETA-LACTAMS .2. A FORMAL SYNTHESIS OF (+/-)-CARPETIMYCIN-A publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BUYNAK, JD – volume: 109 start-page: 1129 year: 1987 ident: WOS:A1987G075700023 article-title: ASYMMETRIC-SYNTHESIS OF (1'R,3R,4R)-4-ACETOXY-3-(1'-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL)-2-AZETIDINONE AND OTHER 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM (S)-(+)-ETHYL 3-HYDROXYBUTANOATE - FORMAL TOTAL SYNTHESIS OF (+)-THIENAMYCIN publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: GEORG, GI – volume: 25 start-page: 1095 year: 1986 ident: WOS:A1986F279600003 article-title: STEREOCHEMICAL ASPECTS OF THE BOSE REACTION FOR ALPHA-AMINO-BETA-LACTAM SYNTHESIS publication-title: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY contributor: fullname: MANHAS, MS – volume: 40 start-page: 309 year: 1987 ident: WOS:A1987G536200009 article-title: ESTER-IMINE CONDENSATIONS - PREPARATION OF RACEMIC INTERMEDIATES FOR THE SYNTHESIS OF THE CARBAPENEM ANTIBIOTICS PS-5 AND PS-6 publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: HA, DC – volume: 102 start-page: 2039 year: 1980 ident: WOS:A1980JJ63500045 article-title: PENEMS, A NEW CLASS OF BETA-LACTAM ANTIBIOTICS .5. TOTAL SYNTHESIS OF RACEMIC "6-ALPHA-HYDROXYETHYLPENEMCARBOXYLIC ACIDS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: PFAENDLER, HR – volume: 26 start-page: 5493 year: 1985 ident: WOS:A1985ATW8500003 article-title: AN ENANTIOSELECTIVE APPROACH TO CARBAPENEM ANTIBIOTICS - FORMAL SYNTHESIS OF (+)-THIENAMYCIN publication-title: TETRAHEDRON LETTERS contributor: fullname: HART, DJ – volume: 26 start-page: 2611 year: 1987 ident: WOS:A1987K229300009 article-title: SYNTHESIS OF 1,3-DIOXIN-4-ONES AND THEIR USE IN SYNTHESIS .14. A NOVEL SYNTHETIC METHOD OF LACTAMS FROM 1,3-DIOXIN-4-ONES VIA INTRAMOLECULAR KETENE TRAPPING publication-title: HETEROCYCLES contributor: fullname: SATO, M – volume: 26 start-page: 5001 year: 1985 ident: WOS:A1985ASG1400010 article-title: SYNTHESIS AND REACTIVITY OF SULFUR AND SILYL SUBSTITUTED ALPHA-ALKYLIDENE-BETA-LACTAMS publication-title: TETRAHEDRON LETTERS contributor: fullname: BUYNAK, JD – start-page: 221 year: 1986 ident: WOS:A1986A151000006 article-title: SIMPLE AND CONDENSED BETA-LACTAMS .5. THE SYNTHESIS OF SOME (5RS,6SR)-2-(2-FORMYLAMINOETHYLTHIO)-6-(2-METHYL-1,3-DIOXOLAN-2-YL)CARBAPENEM-3-CARBOXYLIC ACID-DERIVATIVES AND RELATED-COMPOUNDS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: FETTER, J – start-page: 368 year: 1985 ident: WOS:A1985A122700004 article-title: SIMPLE AND CONDENSED BETA-LACTAMS .6. A SYNTHESIS OF THE P-NITROBENZYL ESTERS OF THE RACEMIC FORMS OF THE CARBAPENEM ANTIBIOTICS PS-5 AND PS-6 AND THEIR 6-EPIMERS publication-title: JOURNAL OF CHEMICAL RESEARCH-S contributor: fullname: FETTER, J – volume: 17 start-page: 496 year: 1982 ident: WOS:A1990CJ67400035.26 publication-title: HETEROCYCLES contributor: fullname: KAMETANI T – volume: 47 start-page: 2765 year: 1982 ident: WOS:A1982NV96100016 article-title: OXIDATIVE N-DEARYLATION OF 2-AZETIDINONES - PARA-ANISIDINE AS A SOURCE OF AZETIDINONE NITROGEN publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KRONENTHAL, DR – start-page: 2031 year: 1974 ident: WOS:A1974T058800026 article-title: NEW TOTAL SYNTHESIS OF (+/-)-DESACETYLCEPHALOTHIN LACTONE SYNTHESIS OF NOVEL FURO[3,4-C] CEPHAMS publication-title: TETRAHEDRON LETTERS contributor: fullname: EDWARDS, JA – volume: 27 start-page: 5955 year: 1986 ident: WOS:A1986F128200013 article-title: A NOVEL CHEMICAL TRANSFORMATION OF 3-VINYL-4-SUBSTITUTED-2-AZETIDINONES - STUDIES ON LACTAMS .77. publication-title: TETRAHEDRON LETTERS contributor: fullname: BOSE, AK – volume: 18 start-page: 486 year: 1975 ident: WOS:A1975W316300009 article-title: PREPARATION AND PROPERTIES OF 5-PHENYLPHENOXYMETHYLPENICILLIN publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: VANDERHAEGHE, H – volume: 50 start-page: 4245 year: 1985 ident: WOS:A1985ATL7700012 article-title: USEFUL CHEMISTRY OF 3-(1-METHYLETHYLIDENE)-4-ACETOXY-2-AZETIDINONE - A FORMAL SYNTHESIS OF (+/-)-ASPARENOMYCIN-C publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BUYNAK, JD – volume: 25 start-page: 3779 year: 1984 ident: WOS:A1984TG45900001 article-title: STEREOSELECTIVE SYNTHESIS OF 3-(1-HYDROXYETHYL)-2-AZETIDINONES FROM 3-HYDROXYBUTYRATES publication-title: TETRAHEDRON LETTERS contributor: fullname: GEORG, GI – volume: 39 start-page: 3384 year: 1974 ident: WOS:A1974U696900017 article-title: TOTAL SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .6. 3-ARYLCEPHALOSPORINS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: FIRESTON.RA – start-page: 809 year: 1988 ident: WOS:A1988P085300032 article-title: A SHORT FORMAL SYNTHESIS OF THE CARBAPENEM ANTIBIOTIC (+/-)-PS-5 publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: ODRIOZOLA, JM – start-page: 5119 year: 1978 ident: WOS:A1978GB23800017 article-title: NOVEL SYNTHESIS OF NOCARDICINS AND THEIR ANALOGS publication-title: TETRAHEDRON LETTERS contributor: fullname: KAMIYA, T – volume: 2 start-page: 101 year: 1982 ident: WOS:A1990CJ67400035.24 publication-title: CHEM BIOL BETA LACTA contributor: fullname: HOLDEN KG – year: 1971 ident: WOS:A1990CJ67400035.30 publication-title: BETA LACTAMS NATURAL contributor: fullname: MANHAS MS |
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Title | STUDIES ON LACTAMS .84. BETA-LACTAMS VIA ALPHA,BETA-UNSATURATED ACID-CHLORIDES - INTERMEDIATES FOR CARBAPENEM ANTIBIOTICS |
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