Serinal-derived vinyl oxiranes as novel and versatile building blocks for the stereoselective synthesis of D- and L-erythro-sphingosines

被引：12

作者：

Hertweck, C

Goerls, H

Boland, W

机构：

[1] Max Planck Inst Chem Ecol, D-07745 Jena, Germany

[2] Univ Jena, Inst Inorgan & Analyt Chem, D-6900 Jena, Germany

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 18期

关键词：

D O I：

10.1039/a804415e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxazolidine vinyl oxirane 1, a novel and highly versatile building block for the preparation of enantiopure D-(+)-erythro-sphingosine and analogues, has been prepared by chloroallylboration of the Garner aldehyde with absolute stereocontrol and in good yield.

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收藏

页码：1955 / 1956

页数：2

相关论文

共 20 条

[1] STEREOCONTROLLED SYNTHESIS OF CALYCULIN-A - CONSTRUCTION OF THE C(26)-C(37) AMIDE OXAZOLE UNIT [J].

BARRETT, AGM ;

EDMUNDS, JJ ;

HENDRIX, JA ;

MALECHA, JW ;

PARKINSON, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1240-1242

[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .35. SIMPLE PROCEDURES FOR THE EFFICIENT RECYCLING OF THE TERPENYL CHIRAL AUXILIARIES AND CONVENIENT ISOLATION OF THE HOMOALLYLIC ALCOHOLS IN ASYMMETRIC ALLYLBORATION AND CROTYLBORATION OF ALDEHYDES [J].

BROWN, HC ;

RACHERLA, US ;

LIAO, Y ;

KHANNA, VV .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6608-6614

[3] 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

[4] 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

[5] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[6] SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE DERIVATIVES FROM L-SERINE [J].

HEROLD, P .

HELVETICA CHIMICA ACTA, 1988, 71 (02) :354-362

[7] Highly efficient synthesis of (+/-)-lamoxirene, the gamete-releasing and gamete-attracting pheromone of the Laminariales (Phaeophyta) [J].

Hertweck, C ;

Boland, W .

TETRAHEDRON, 1997, 53 (43) :14651-14654

[8]

Igarashi Y, 1997, J BIOCHEM-TOKYO, V122, P1080

[9]

JAYARAMAN S, 1995, TETRAHEDRON LETT, V36, P4765

[10] THE RATE OF BULK FLOW FROM THE GOLGI TO THE PLASMA-MEMBRANE [J].

KARRENBAUER, A ;

JECKEL, D ;

JUST, W ;

BIRK, R ;

SCHMIDT, RR ;

ROTHMAN, JE ;

WIELAND, FT .

CELL, 1990, 63 (02) :259-267