A GENERAL WAY, FROM L-ASCORBIC AND D-ISOASCORBIC ACIDS, TO HOMOCHIRAL ALPHA-HYDROXY, ALPHA,BETA-DIHYDROXY AND ALPHA,BETA-EPOXY-ALDEHYDES, USEFUL BUILDING-BLOCKS FOR THE SYNTHESIS OF LINEAR OXYGENATED FATTY-ACIDS METABOLITES

被引：27

作者：

GRAVIERPELLETIER, C

DUMAS, J

LEMERRER, Y

DEPEZAY, JC

机构：

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1992年 / 11卷 / 08期

关键词：

D O I：

10.1080/07328303.1992.11760692

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Enantiomerically pure alpha-hydroxy, alpha,beta-dihydroxy and alpha,beta-epoxyaldehydes, useful building blocks for the synthesis of acyclic oxygenated fatty acids metabolites, were synthetized via epoxybutanediol acetonide starting from the commercially available L-ascorbic and D-isoascorbic acids.

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页码：969 / 998

页数：30

相关论文

共 31 条

[1] THE CHEMISTRY OF L-ASCORBIC AND D-ISOASCORBIC ACIDS .1. THE PREPARATION OF CHIRAL BUTANETRIOLS AND BUTANETETROLS [J].

ABUSHANAB, E ;

VEMISHETTI, P ;

LEIBY, RW ;

SINGH, HK ;

MIKKILINENI, AB ;

WU, DCJ ;

SAIBABA, R ;

PANZICA, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2598-2602

[2] PRACTICAL ENANTIOSPECIFIC SYNTHESES OF (+) ERYTHRO-9-(2S-HYDROXY-3R-NONYL) ADENINE [J].

ABUSHANAB, E ;

BESSODES, M ;

ANTONAKIS, K .

TETRAHEDRON LETTERS, 1984, 25 (35) :3841-3844

[3] TRANSFORMATIONS OF TARTARIC ACID - A FACILE SYNTHESIS OF DERIVATIVES OF OPTICALLY-ACTIVE ALPHA-HYDROHYALDEHYDES [J].

ACHMATOWICZ, B ;

WICHA, J .

TETRAHEDRON LETTERS, 1987, 28 (26) :2999-3002

[4] ENANTIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF LIPOXIN-A - STEREOCHEMICAL ASSIGNMENT OF THE NATURAL LIPOXIN-A AND ITS POSSIBLE BIOSYNTHESIS [J].

ADAMS, J ;

FITZSIMMONS, BJ ;

GIRARD, Y ;

LEBLANC, Y ;

EVANS, JF ;

ROKACH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :464-469

[5]

ALHAKIM AH, 1985, SYNTHESIS-STUTTGART, P207

[6] SYNTHETIC STUDIES ON SPIRODILACTONES .2. INVESTIGATION OF USE OF L-ASCORBIC-ACID AND ITS DERIVATIVES IN SYNTHESIS OF SPIRODILACTONES [J].

BRIMACOMBE, JS ;

MURRAY, AW ;

ZAHURULHAQUE .

CARBOHYDRATE RESEARCH, 1975, 45 (DEC) :45-53

[7] ENANTIOSPECIFIC SYNTHESES OF LEUKOTRIENE-C4, LEUKOTRIENE-D4, AND LEUKOTRIENE-E4 AND [14,15-H-3(2)]LEUKOTRIENE-E4 DIMETHYL ESTER [J].

COHEN, N ;

BANNER, BL ;

LOPRESTI, RJ ;

WONG, F ;

ROSENBERGER, M ;

LIU, YY ;

THOM, E ;

LIEBMAN, AA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3661-3672

[8]

COREY EJ, 1984, LEUKOTRIENES CHEM BI, P13

[9] SORBIC ACID IRON TRICARBONYL COMPLEX AS RESOLVING AGENT - CHIRAL SYNTHESES OF 4-HYDROXY NONENAL AND CORIOLIC ACID [J].

DEMONTARBY, L ;

MOSSET, P ;

GREE, R .

TETRAHEDRON LETTERS, 1988, 29 (32) :3937-3940

[10]

GRAVIERPELLETIER C, 1990, PROG LIPID RES, V29, P229

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