A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation

被引：60

作者：

Imashiro, R ^{[1
]}

Sakurai, O ^{[1
]}

Yamashita, T ^{[1
]}

Horikawa, H ^{[1
]}

机构：

[1] Tanabe Seiyaku Co Ltd, Discovery Res Lab, Yodogawa, Osaka 5328505, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(98)00615-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of the phytosphingosine derivatives and their stereoisomers by using asymmetric dihydroxylation of the optically active olefins derived from L-serine is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10657 / 10670

页数：14

共 35 条

[1] UTILIZATION AND DEGRADATION OF PHYTOSPHINGOSINE BY RAT LIVER [J].

BARENHOLZ, Y ;

GATT, S .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1967, 27 (03) :319-+

[2] SYNTHESIS OF CHIRAL VINYLGLYCINES [J].

BEAULIEU, PL ;

DUCEPPE, JS ;

JOHNSON, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4196-4204

[3] ACYCLIC STEREOCONTROL INDUCED BY ALLYLIC ALKOXY GROUPS - SYNTHETIC APPLICATIONS OF STEREOSELECTIVE DIHYDROXYLATION IN NATURAL PRODUCT SYNTHESIS [J].

CHA, JK ;

KIM, NS .

CHEMICAL REVIEWS, 1995, 95 (06) :1761-1795

[4] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON LETTERS, 1983, 24 (37) :3943-3946

[5] ON STEREOCHEMISTRY OF OSMIUM-TETROXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EXAMPLES [J].

CHRIST, WJ ;

CHA, JK ;

KISHI, Y .

TETRAHEDRON LETTERS, 1983, 24 (37) :3947-3950

[6] Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate [J].

Cuvillier, O ;

Pirianov, G ;

Kleuser, B ;

Vanek, PG ;

Coso, OA ;

Gutkind, JS ;

Spiegel, S .

NATURE, 1996, 381 (6585) :800-803

[7] 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

[8]

Garner P., 1991, ORG SYNTH, V70, P18

[9] A SYNTHESIS OF PHYTOSPHINGOSINES FROM D-GALACTOSE [J].

GIGG, J ;

GIGG, R .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (20) :1876-&

[10] A SYNTHESIS OF PHYTOSPINGOSINES FORM D-GLUCOSAMINE [J].

GIGG, J ;

GIGG, R ;

WARREN, CD .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (20) :1872-+

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