SYNTHESIS OF CHIRAL LONG-CHAIN ALPHA-HYDROXY ACIDS FROM L-ASCORBIC-ACID - USEFUL COMPONENTS FOR THE SYNTHESIS OF CEREBROSIDES

被引：11

作者：

YAMAGATA, K ^{[1
]}

YAMAGIWA, Y ^{[1
]}

KAMIKAWA, T ^{[1
]}

机构：

[1] KINKI UNIV,FAC SCI & TECHNOL,DEPT CHEM,OSAKA,OSAKA 577,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 12期

关键词：

D O I：

10.1039/p19900003355

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic ring opening of chiral epoxy diols, derived from L-ascorbic acid, with 2-lithio-1,3-dithianes allowed preparation of long-chain (R)- and (S)-alpha-hydroxy acids of high optical purity.

引用

页码：3355 / 3357

页数：3

共 21 条

[11] CHIRAL ALPHA-HYDROXY-AND ALPHA,BETA-DIHYDROXY-ALDEHYDES FROM D-ISOASCORBIC AND L-ASCORBIC ACIDS - USEFUL PRECURSORS FOR THE SYNTHESIS OF FATTY-ACID METABOLITES [J].

LEMERRER, Y ;

GRAVIERPELLETIER, C ;

DUMAS, J ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1990, 31 (07) :1003-1006

[12] ELECTROPHILIC ASYMMETRIC SYNTHESES OF ALPHA-HYDROXY CARBOXYLIC-ACIDS [J].

LUDWIG, JW ;

NEWCOMB, M ;

BERGBREITER, DE .

TETRAHEDRON LETTERS, 1986, 27 (24) :2731-2734

[13] EASY AND GENERAL-METHOD TO SYNTHESIZE CHIRAL 2-HYDROXYACID BENZOATES [J].

MARTIN, VS ;

NUNEZ, MT ;

TONN, CE .

TETRAHEDRON LETTERS, 1988, 29 (22) :2701-2702

[14]

MASTUBARA T, 1989, 16TH INT S CHEM NAT

[15] ASYMMETRIC ADDITION OF ORGANOMETALLICS TO CHIRAL KETOOXAZOLINES - PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXY ACIDS [J].

MEYERS, AI ;

SLADE, J .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (14) :2785-2791

[16] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[17] SYNTHESIS OF SPHINGOSINE RELATIVES .2. SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-9-METHYL-4,8-SPHINGADIENINE, THE CERAMIDE PORTION OF THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM-COMMUNE, AND ITS (2R,3S)-ISOMER [J].

MORI, K ;

FUNAKI, Y .

TETRAHEDRON, 1985, 41 (12) :2369-2377

[18] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .6. STEREOCHEMICAL CONTROL ON YEAST REDUCTION OF ALPHA-KETO ESTERS - REDUCTION BY IMMOBILIZED BAKERS-YEAST IN HEXANE [J].

NAKAMURA, K ;

INOUE, K ;

USHIO, K ;

OKA, S ;

OHNO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2589-2593

[19] A HIGHLY STEREOSELECTIVE CONVERSION OF ALPHA,BETA-EPOXY ESTERS TO ALPHA-HYDROXY ESTERS - AN EFFICIENT ROUTE TO OPTICALLY-ACTIVE ALPHA-HYDROXYESTERS [J].

OTSUBO, K ;

INANAGA, J ;

YAMAGUCHI, M .

TETRAHEDRON LETTERS, 1987, 28 (38) :4435-4436

[20]

PEARSON WH, 1986, J ORG CHEM, V51, P3476

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