A facile synthesis of N-protected statine and analogs via a lipase-catalyzed kinetic resolution
A new synthesis of N-protected statine 4a and its analogue 4b is presented. cis-(+/-)-Butyric acid 2-isobutyl-5-oxopyrrolidin-3-yl ester (10a) and cis-(+/-)-butyric acid 2-benzyl-5-oxopyrrolidin-3-yl ester (10b) were prepared from methyl (E)-4-chloro-3-methoxybut-2-enoate (5) and subsequently resolv...
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| Published in | Journal of organic chemistry Vol. 58; no. 15; pp. 4010 - 4012 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.07.1993
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A new synthesis of N-protected statine 4a and its analogue 4b is presented. cis-(+/-)-Butyric acid 2-isobutyl-5-oxopyrrolidin-3-yl ester (10a) and cis-(+/-)-butyric acid 2-benzyl-5-oxopyrrolidin-3-yl ester (10b) were prepared from methyl (E)-4-chloro-3-methoxybut-2-enoate (5) and subsequently resolved via a kinetic resolution catalyzed by Candida Cylindracea lipase. The desired enantiomers were isolated in excellent enantiomeric excess and good yield. These products were then converted to the N-BOC-protected hydroxy amino acids 4a and 4b. |
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| AbstractList | A new synthesis of N-protected statine 4a and its analogue 4b is presented. cis-(+/-)-Butyric acid 2-isobutyl-5-oxopyrrolidin-3-yl ester (10a) and cis-(+/-)-butyric acid 2-benzyl-5-oxopyrrolidin-3-yl ester (10b) were prepared from methyl (E)-4-chloro-3-methoxybut-2-enoate (5) and subsequently resolved via a kinetic resolution catalyzed by Candida Cylindracea lipase. The desired enantiomers were isolated in excellent enantiomeric excess and good yield. These products were then converted to the N-BOC-protected hydroxy amino acids 4a and 4b. |
| Author | Baenziger, Markus McGarrity, John F Meul, Thomas |
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| Keywords | ORGANIC-SYNTHESIS ASYMMETRIC-SYNTHESIS (3S,4S)-STATINE AMINO EFFICIENT SYNTHESIS STEREOSPECIFIC SYNTHESIS TETRAMIC-ACID STEREOSELECTIVE SYNTHESIS RENIN INHIBITORS (3S,4S)-CYCLOHEXYLSTATINE Fungi Candida cylindracea α-Aminoacid Hydroxyacid Enzyme Aliphatic compound Optical resolution Trans stereoisomer Triacylglycerol lipase Fungi Imperfecti Thallophyta Enzymatic reaction |
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| References_xml | – volume: 31 start-page: 1803 year: 1990 ident: WOS:A1990CY56400006 article-title: ADDITION OF ALLYLIC METALS TO ALPHA-AMINOALDEHYDES - APPLICATION TO THE SYNTHESIS OF STATINE, KETOMETHYLENE AND HYDROXYETHYLENE DIPEPTIDE ISOSTERES publication-title: TETRAHEDRON LETTERS contributor: fullname: PRASAD, JVNV – volume: 16 start-page: 37 year: 1991 ident: BCI:BCI199140087583 article-title: RENIN ANGIOTENSIN SYSTEM RAS DEPENDENT ANTIHYPERTENSIVE AGENTS I. RENIN INHIBITORS publication-title: Drugs of the Future contributor: fullname: OCAIN T D – start-page: 457 year: 1990 ident: WOS:A1990DH84100005 article-title: SHORT AND EFFICIENT SYNTHESIS OF STATINE AND ISOSTATINE DERIVATIVES publication-title: SYNTHESIS-STUTTGART contributor: fullname: KESSLER, H – start-page: 391 year: 1992 ident: WOS:A1992HP49200018 article-title: METHYL (E)-4-CHLORO-3-METHOXY-2-BUTENOATE - AN EXTREMELY VERSATILE 4-CARBON BUILDING BLOCK publication-title: SYNTHESIS-STUTTGART contributor: fullname: DUC, L – volume: 49 start-page: 3287 year: 1976 ident: WOS:A1976CM66800084 article-title: STEREOSELECTIVE SYNTHESIS OF THREO-3-HYDROXY-4-AMINO ACIDS publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: KATSUKI, T – start-page: 373 year: 1992 ident: WOS:A1992HP49200012 article-title: A SIMPLE SYNTHESIS OF 1,3-CYCLOPENTANEDIONE publication-title: SYNTHESIS-STUTTGART contributor: fullname: FUCHS, R – volume: 75 start-page: 892 year: 1992 ident: WOS:A1992HU38700022 article-title: AN EFFICIENT SYNTHESIS OF RACEMIC 4-HYDROXY-2-OXO-1-PYRROLIDINEACETAMIDE (OXIRACETAM) USING TETRAMIC-ACID INTERMEDIATES publication-title: HELVETICA CHIMICA ACTA contributor: fullname: LAFFAN, DDP – start-page: 179 year: 1986 ident: WOS:A1993LV42400038.32 publication-title: PROTEINASE INHIBITOR contributor: fullname: RICH DH – volume: 29 start-page: 2307 year: 1988 ident: WOS:A1988N440400009 article-title: A NOVEL SHORT AND EFFICIENT ASYMMETRIC-SYNTHESIS OF STATINE ANALOGS publication-title: TETRAHEDRON LETTERS contributor: fullname: DEVANT, RM – volume: 54 start-page: 513 year: 1989 ident: WOS:A1989T155900001 article-title: NEW DIASTEREOSELECTIVE SYNTHESIS OF OXAZOLIDIN-2-ONES THROUGH CARBON CARBON BOND FORMATION ON CYCLIC CARBAMOYLOXY RADICALS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KANO, S – volume: 39 start-page: 2425 year: 1991 ident: WOS:A1991GJ95200044 article-title: A HIGHLY STEREOSELECTIVE SYNTHESIS OF (3S,4S)-STATINE AND (3S,4S)-CYCLOHEXYLSTATINE publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: TAKEMOTO, Y – start-page: 216 year: 1993 ident: WOS:A1993KN23400012 article-title: ENANTIOSELECTIVE AND DIASTEREOSELECTIVE FORMATION OF SYN-3-HYDROXY-4-AMINO ACIDS (SYN-STATINES) VIA TETRAMIC ACIDS publication-title: SYNTHESIS-STUTTGART contributor: fullname: SCHMIDT, U – start-page: 951 year: 1989 ident: WOS:A1989CD11500019 article-title: SYNTHESIS OF N-BOC-STATINE AND EPI-STATINE publication-title: SYNTHESIS-STUTTGART contributor: fullname: WUTS, PGM – volume: 28 start-page: 1779 year: 1985 ident: WOS:A1985AVH8900007 article-title: RENIN INHIBITORS - SYNTHESES OF SUBNANOMOLAR, COMPETITIVE, TRANSITION-STATE ANALOG INHIBITORS CONTAINING A NOVEL ANALOG OF STATINE publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: BOGER, J – start-page: 1474 year: 1989 ident: WOS:A1989AV66200040 article-title: A SIMPLE SYNTHETIC ROUTE TO STATINE AND STATINE ANALOGS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: REETZ, MT – volume: 56 start-page: 2050 year: 1991 ident: WOS:A1991FC94700017 article-title: OPTICALLY-ACTIVE BUILDING-BLOCKS FROM THE SPAC REACTION - A COMPLETELY ASYMMETRIC-SYNTHESIS OF (4S-CIS)-5-(CYCLOHEXYLMETHYL)-4-HYDROXY-2-PYRROLIDINONE, A STATINE ANALOG publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BURGESS, K – volume: 32 start-page: 3523 year: 1991 ident: WOS:A1991FU58800022 article-title: LEWIS ACID-PROMOTED DIRECT SUBSTITUTION OF 4-METHOXY-2-OXAZOLIDINONES AND 4-PHENYLTHIO-2-OXAZOLIDINONES BY ALKYL CUPRATES - FACILE PREPARATION OF (3S,4S)-STATINE AND (3S,4S)-CYCLOHEXYLSTATINE publication-title: TETRAHEDRON LETTERS contributor: fullname: ISHIBUCHI, S – volume: 53 start-page: 873 year: 1988 ident: WOS:A1988M259700036 article-title: A SHORT AND EFFICIENT SYNTHESIS OF (3S,4S)-4-[(TERT-BUTYLOXYCARBONYL)AMINO]-5-CYCLOHEXYL-3-HYDROXYPENTANOIC ACID ETHYL-ESTER publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SCHUDA, PF – volume: 109 start-page: 236 year: 1987 ident: WOS:A1987F589700035 article-title: CONFIGURATIONAL STABILITY OF N-PROTECTED ALPHA-AMINO ALDEHYDES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LUBELL, WD – volume: 31 start-page: 7359 year: 1990 ident: WOS:A1990EN60200031 article-title: A STEREOSELECTIVE SYNTHESIS OF (3S,4S) STATINE AND RELATED-COMPOUNDS publication-title: TETRAHEDRON LETTERS contributor: fullname: MISITI, D – volume: 100 start-page: 414 year: 1988 ident: WOS:A1993LV42400038.30 publication-title: ANGEW CHEM contributor: fullname: RADDATZ P – start-page: 2121 year: 1972 ident: WOS:A1972N534500002 article-title: SYNTHESIS OF PYRROLIDINE-2,4-DIONES (TETRAMIC ACIDS) AND SOME DERIVATIVES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: MULHOLLAND, TP – volume: 36 start-page: 756 year: 1988 ident: WOS:A1993LV42400038.1 publication-title: NACHR CHEM TECH LAB contributor: fullname: ALTENBACH HJ – volume: 38 start-page: 103 year: 1990 ident: WOS:A1990CP13600020 article-title: SYNTHESES AND BIOLOGICAL-ACTIVITIES OF RENIN INHIBITORS CONTAINING STATINE ANALOGS publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: NISHI, T – volume: 1 start-page: 721 year: 1990 ident: WOS:A1990EH30700010 article-title: ENZYMES IN ORGANIC-SYNTHESIS - REMARKABLE INFLUENCE OF A PI-SYSTEM ON THE ENANTIOSELECTIVITY IN PPL CATALYZED MONOHYDROLYSIS OF 2-SUBSTITUTED 1,3-DIACETOXYPROPANES publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: GUANTI, G – volume: 112 start-page: 1150 year: 1990 ident: WOS:A1990CM13700040 article-title: SYNTHESES AND REACTIONS OF SILYL CARBAMATES .2. A NEW MODE OF CYCLIC CARBAMATE FORMATION FROM TERT-BUTYLDIMETHYLSILYL CARBAMATE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: SAKAITANI, M – volume: 34 start-page: 223 year: 1978 ident: WOS:A1978EJ49900012 article-title: TOTAL SYNTHESIS OF ANTIBIOTIC MALONOMICIN (K16) publication-title: TETRAHEDRON contributor: fullname: VANDERBAAN, JL – volume: 19 start-page: 2573 year: 1989 ident: WOS:A1989AQ75800039 article-title: STEREOSPECIFIC SYNTHESIS OF S,S-STATINE AND ITS CONGENERS publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: KLUTCHKO, S – volume: 53 start-page: 869 year: 1988 ident: WOS:A1988M259700035 article-title: A FACILE SYNTHESIS OF STATINE AND ANALOGS BY REDUCTION OF BETA-KETO-ESTERS DERIVED FROM BOC-PROTECTED AMINO-ACIDS - HPLC ANALYSES OF THEIR ENANTIOMERIC PURITY publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MAIBAUM, J – volume: 55 start-page: 3947 year: 1990 ident: WOS:A1990DH23300045 article-title: A FACILE SYNTHESIS OF N-PROTECTED STATINE AND ITS ANALOG VIA STEREOSELECTIVE IODOLACTAMIZATION publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: TAKAHATA, H – volume: 30 start-page: 2697 year: 1989 ident: WOS:A1989U912700027 article-title: ENZYMES AS SELECTIVE REAGENTS IN ORGANIC-SYNTHESIS - ENANTIOSELECTIVE PREPARATION OF ASYMMETRIZED TRIS(HYDROXYMETHYL)METHANE publication-title: TETRAHEDRON LETTERS contributor: fullname: GUANTI, G – volume: 23 start-page: 259 year: 1970 ident: WOS:A1970G575600010 article-title: PEPSTATIN, A NEW PEPSIN INHIBITOR PRODUCED BY ACTINOMYCETES publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: UMEZAWA, H – volume: 29 start-page: 6327 year: 1988 ident: WOS:A1988R318000035 article-title: SYNTHESIS OF STATINE AND ITS ANALOGS BY HOMOGENEOUS ASYMMETRIC HYDROGENATION publication-title: TETRAHEDRON LETTERS contributor: fullname: NISHI, T – volume: 32 start-page: 401 year: 1991 ident: WOS:A1991ET81500028 article-title: SYNTHESIS OF STATINE FROM (S)-MALIC ACID - STEREOCONTROL VIA RADICAL CYCLIZATION publication-title: TETRAHEDRON LETTERS contributor: fullname: KOOT, WJ – volume: 31 start-page: 4949 year: 1990 ident: WOS:A1990DV03700037 article-title: STEREOSELECTIVE SYNTHESIS OF STATIN ANALOGS publication-title: TETRAHEDRON LETTERS contributor: fullname: BERNARDI, A – volume: 31 start-page: 7329 year: 1990 ident: WOS:A1990EN60200021 article-title: DIASTEREOSPECIFIC SYNTHESIS OF (-)-STATINE publication-title: TETRAHEDRON LETTERS contributor: fullname: OHTA, T – volume: 63 start-page: 160 year: 1985 ident: WOS:A1993LV42400038.14 publication-title: ORG SYNTH contributor: fullname: KELLER O – volume: 1 start-page: 421 year: 1990 ident: WOS:A1990DR17800002 article-title: ASYMMETRIZATION OF 2-SUBSTITUTED GLYCEROLS - SYNTHESES OF R-ETOMOXIR AND R-PALMOXIRATE publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: PRASAD, K – start-page: 1177 year: 1987 ident: WOS:A1987H772200002 article-title: STEREOSPECIFIC SYNTHESIS OF N-PROTECTED STATINE AND ITS ANALOGS VIA CHIRAL TETRAMIC ACID publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: JOUIN, P – volume: 111 start-page: 4368 year: 1989 ident: WOS:A1989AB03100033 article-title: STEREOSELECTIVE SYNTHESES OF ERYTHRO-BETA-AMINO AND THREO-BETA-AMINO ALCOHOL DERIVATIVES VIA HETERO-DIELS-ALDER REACTIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MIDLAND, MM |
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| Snippet | A new synthesis of N-protected statine 4a and its analogue 4b is presented. cis-(+/-)-Butyric acid 2-isobutyl-5-oxopyrrolidin-3-yl ester (10a) and... |
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| SubjectTerms | Aliphatic compounds Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Chemistry Chemistry, Organic Exact sciences and technology Fundamental and applied biological sciences. Psychology Methods. Procedures. Technologies Organic chemistry Physical Sciences Preparations and properties Science & Technology |
| Title | A facile synthesis of N-protected statine and analogs via a lipase-catalyzed kinetic resolution |
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