A new diorganozinc-based enantioselective access to truncated D-ribo-phytosphingosine

被引：10

作者：

Ayad, T ^{[1
]}

Génisson, Y ^{[1
]}

Verdu, A ^{[1
]}

Baltas, M ^{[1
]}

Gorrichon, L ^{[1
]}

机构：

[1] Univ Toulouse 3, UMR 5068, LSPCMIB, F-31062 Toulouse, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 03期

关键词：

phytosphingosine; diorganozinc reagent; double asymmetric induction;

D O I：

10.1016/S0040-4039(02)02526-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of a trans alpha,beta-epoxyaldehyde as a precursor Of D-ribo-phytosphingosines was studied. The highly stereoselective alkylation of the aldehyde with a diorganozinc reagent was ensured through double asymmetric induction. The regioselective opening of the epoxide in turn gives access to an azide from which a C-10 phytosphingosine can be easily prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：579 / 582

页数：4

共 41 条

[1] Stereospecific total syntheses of sphingosine and its analogues from L-serine [J].

Azuma, H ;

Tamagaki, S ;

Ogino, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3538-3541

[2] SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 [J].

BEHRENS, CH ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5696-5704

[3] REGIOSELECTIVE AZIDE OPENING OF 2,3-EPOXY ALCOHOLS BY [TI(O-I-PR)2(N3)2] - SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

CARON, M ;

CARLIER, PR ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5185-5187

[4]

CARTER HE, 1954, J BIOL CHEM, V206, P613

[5] Synthesis of ceramide analogues having the C(4)-C(5) bond of the long-chain base as part of an aromatic or heteroaromatic system [J].

Chun, J ;

He, LL ;

Byun, HS ;

Bittman, R .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) :7634-7640

[6] DIASTEREOFACE DIFFERENTIATION IN ADDITION OF LITHIUM ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES [J].

ESCUDIER, JM ;

BALTAS, M ;

GORRICHON, L .

TETRAHEDRON, 1993, 49 (24) :5253-5266

[7] Double stereodifferentiation in asymmetric dihydroxylation:: application to the first diastereoselective synthesis of L-xylo-[2R,3S,4S]-C18-phytosphingosine [J].

Fernandes, RA ;

Kumar, P .

TETRAHEDRON LETTERS, 2000, 41 (52) :10309-10312

[8] Total synthesis of α-galactosyl cerebroside [J].

Figueroa-Pérez, S ;

Schmidt, RR .

CARBOHYDRATE RESEARCH, 2000, 328 (02) :95-102

[9] α-Galactosylceramide-activated Vα14 natural killer T cells mediate protection against murine malaria [J].

Gonzalez-Aseguinolaza, G ;

de Oliveira, C ;

Tomaska, M ;

Hong, S ;

Bruna-Romero, O ;

Nakayama, T ;

Taniguchi, M ;

Bendelac, A ;

Van Kaer, L ;

Koezuka, Y ;

Tsuji, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (15) :8461-8466

[10] 2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis [J].

Graziani, A ;

Passacantilli, P ;

Piancatelli, G ;

Tani, S .

TETRAHEDRON-ASYMMETRY, 2000, 11 (19) :3921-3937

← 1 2 3 4 5 →