A short highly stereoselective synthesis of the fluorinated natural product (2S,3S)-4-fluorothreonine
A three step stereoselective route to the fluorinated natural product (2S,3S)-4-fluorothreonine is described; the route is amenable to the preparation of (2S,3S)-4-fluoro[3-H-2]threonine and (2S,3R)-[4,4,4-H-2(3)] threonine.
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| Published in | Chemical communications (Cambridge, England) no. 15; pp. 1471 - 1472 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
1997
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| Subjects | |
| Online Access | Get full text |
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| Abstract | A three step stereoselective route to the fluorinated natural product (2S,3S)-4-fluorothreonine is described; the route is amenable to the preparation of (2S,3S)-4-fluoro[3-H-2]threonine and (2S,3R)-[4,4,4-H-2(3)] threonine. |
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| AbstractList | A three step stereoselective route to the fluorinated natural product (2S,3S)-4-fluorothreonine is described; the route is amenable to the preparation of (2S,3S)-4-fluoro[3-H-2]threonine and (2S,3R)-[4,4,4-H-2(3)] threonine. |
| Author | OHagan, D Amin, MR Moloney, JM Harper, DB Murphy, CD Howard, JAK |
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| Keywords | ENANTIOSELECTIVE SYNTHESIS ACIDS BIOSYNTHESIS STREPTOMYCES-CATTLEYA ALDEHYDES DERIVATIVES THREONINE |
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| References | BLASER, D (WOS:A1991GN36800015) 1991 SAUNDERS, BC (WOS:A1949UB64700001) 1949 SCOLASTICO, C (WOS:A1985ARK8000003) 1985 Nieschalk, J (WOS:A1997WX45100034) 1997 SANADA, M (WOS:A1986A207200010) 1986; 39 SEEBACH, D (WOS:A1987F977100028) 1987; 70 OHAGAN, D (WOS:A1994PE49800007) 1994; 34 SEEBACH, D (WOS:A1985ABZ5600017) 1985; 68 TEUTSCH, G (WOS:A1984SK45200010) 1984; 25 REID, KA (WOS:A1995RE70400014) 1995; 141 SHIMIZU, M (WOS:A1993LE56000012) 1993; 4 Hamilton, JTG (WOS:A1997WX45100033) 1997 |
| References_xml | – start-page: 1067 year: 1991 ident: WOS:A1991GN36800015 article-title: BENZYL (R) AND (S)-2-TERT-BUTYL-5-OXO-OXAZOLIDINE-3-CARBOXYLATE FOR CONVENIENT PREPARATION OF D-THREONINE AND L-THREONINE ANALOGS FROM ALDEHYDES publication-title: LIEBIGS ANNALEN DER CHEMIE contributor: fullname: BLASER, D – start-page: 850 year: 1985 ident: WOS:A1985ARK8000003 article-title: DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF FLUORINATED THREONINES publication-title: SYNTHESIS-STUTTGART contributor: fullname: SCOLASTICO, C – start-page: 799 year: 1997 ident: WOS:A1997WX45100034 article-title: Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. The stereochemical processing of glycerol publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Nieschalk, J – volume: 34 start-page: 871 year: 1994 ident: WOS:A1994PE49800007 article-title: EFFICIENT ROUTES TO ISOTOPICALLY LABELED EPICHLOROHYDRINS ((CHLOROMETHYL) OXIRANES) publication-title: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS contributor: fullname: OHAGAN, D – volume: 39 start-page: 259 year: 1986 ident: WOS:A1986A207200010 article-title: BIOSYNTHESIS OF FLUOROTHREONINE AND FLUOROACETIC ACID BY THE THIENAMYCIN PRODUCER, STREPTOMYCES-CATTLEYA publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: SANADA, M – volume: 68 start-page: 144 year: 1985 ident: WOS:A1985ABZ5600017 article-title: ALPHA-ALKYLATION OF AMINO-ACIDS WITHOUT RACEMIZATION. PREPARATION OF EITHER (S)-ALPHA-METHYLDOPA OR (R)-ALPHA-METHYLDOPA FROM (S)-ALANINE publication-title: HELVETICA CHIMICA ACTA contributor: fullname: SEEBACH, D – start-page: 773 year: 1949 ident: WOS:A1949UB64700001 article-title: TOXIC FLUORINE COMPOUNDS CONTAINING THE C-F LINK .2. 2-FLUOROETHANOL AND ITS DERIVATIVES publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: SAUNDERS, BC – volume: 70 start-page: 237 year: 1987 ident: WOS:A1987F977100028 article-title: ADDITION OF CHIRAL GLYCINE, METHIONINE, AND VINYLGLYCINE ENOLATE DERIVATIVES TO ALDEHYDES AND KETONES IN THE PREPARATION OF ENANTIOMERICALLY PURE ALPHA-AMINO-BETA-HYDROXY ACIDS publication-title: HELVETICA CHIMICA ACTA contributor: fullname: SEEBACH, D – volume: 141 start-page: 1385 year: 1995 ident: WOS:A1995RE70400014 article-title: BIOSYNTHESIS OF FLUORINATED SECONDARY METABOLITES BY STREPTOMYCES-CATTLEYA publication-title: MICROBIOLOGY-SGM contributor: fullname: REID, KA – volume: 25 start-page: 1561 year: 1984 ident: WOS:A1984SK45200010 article-title: AN ENANTIOSELECTIVE SYNTHESIS OF A 4-FLUOROMETHYL-AZETIDINONE publication-title: TETRAHEDRON LETTERS contributor: fullname: TEUTSCH, G – volume: 4 start-page: 835 year: 1993 ident: WOS:A1993LE56000012 article-title: STEREODIVERGENT SYNTHESIS OF FLUORINATED THREONINE DERIVATIVES IN HIGH OPTICAL PURITY publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: SHIMIZU, M – start-page: 797 year: 1997 ident: WOS:A1997WX45100033 article-title: Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. Glycine and pyruvate as precursors publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Hamilton, JTG |
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| Title | A short highly stereoselective synthesis of the fluorinated natural product (2S,3S)-4-fluorothreonine |
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