HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF D-THREO-SPHINGOSINE AND D-ERYTHRO-SPHINGOSINE FROM GLYCIDOL

被引：19

作者：

KATSUMURA, S

YAMAMOTO, N

FUKUDA, E

IWAMA, S

机构：

来源：

CHEMISTRY LETTERS | 1995年 / 05期

关键词：

D O I：

10.1246/cl.1995.393

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

D-Threo- and D-erythro-sphingosine, (1) and (2), inhibitors of protein kinase C, have been efficiently synthesized from glycidol through (R)-4-methoxycarbonyloxazolidinone (3) by selective mono-alkylation followed by highly diastereoselective reduction of the tin-substituted pentadecenyl ketone 5.

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页码：393 / 394

页数：2

相关论文

共 14 条

[1] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES [J].

DONDONI, A ;

FANTIN, G ;

FOGAGNOLO, M ;

PEDRINI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1439-1446

[2] A STEREODIVERGENT SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE FROM L-SERINE [J].

GARNER, P ;

PARK, JM ;

MALECKI, E .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4395-4398

[3]

HAKOMORI S, 1986, SCI AM, V254, P32

[4] FUNCTIONS OF SPHINGOLIPIDS AND SPHINGOLIPID BREAKDOWN PRODUCTS IN CELLULAR-REGULATION [J].

HANNUN, YA ;

BELL, RM .

SCIENCE, 1989, 243 (4890) :500-507

[5]

HERALD P, 1988, HELV CHIM ACTA, V71, P354

[6] A CONVENIENT STEREOSELECTIVE SYNTHESIS OF D-ERYTHRO-C-18-SPHINGOSINE FROM GALACTAL [J].

HIRATA, N ;

YAMAGIWA, Y ;

KAMIKAWA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2279-2280

[7]

KOSKINEN AMP, 1990, SYNLETT, P665

[8] STRUCTURAL REQUIREMENTS FOR LONG-CHAIN (SPHINGOID) BASE INHIBITION OF PROTEIN KINASE-C INVITRO AND FOR THE CELLULAR EFFECTS OF THESE COMPOUNDS [J].

MERRILL, AH ;

NIMKAR, S ;

MENALDINO, D ;

HANNUN, YA ;

LOOMIS, C ;

BELL, RM ;

TYAGI, SR ;

LAMBETH, JD ;

STEVENS, VL ;

HUNTER, R ;

LIOTTA, DC .

BIOCHEMISTRY, 1989, 28 (08) :3138-3145

[9] TOTAL SYNTHESIS OF (+)-ERYTHRO-N-LAUROYLDOCOSASPHINGA-4,8-DIENINE FROM ANEMONIA-SULCATA AND DETERMINATION OF THE ABSOLUTE-CONFIGURATION [J].

NAKAGAWA, M ;

TSURUOKA, A ;

YOSHIDA, J ;

HINO, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (08) :603-605

[10] A STEREOSELECTIVE SYNTHESIS OF SPHINGOSINE, A PROTEIN KINASE-C INHIBITOR [J].

NIMKAR, S ;

MENALDINO, D ;

MERRILL, AH ;

LIOTTA, D .

TETRAHEDRON LETTERS, 1988, 29 (25) :3037-3040