Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: asymmetric synthesis of 1-deoxynojirimycin

被引：52

作者：

Comins, DL ^{[1
]}

Fulp, AB ^{[1
]}

机构：

[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 39期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(01)01432-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of 1-deoxynojirimycin (2) mediated by a chiral auxiliary is reported. The dihydropyridone 4 was converted to diol 11 in three steps by acetoxylation, hydrolysis, and stereoselective reduction. Dihydroxylation of 11 followed by catalytic reduction afforded 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6839 / 6841

页数：3

共 18 条

[1]

[Anonymous], 1996, Adv. Nitrogen Heterocycl

[2] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[3] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255

[4]

Comins D.L., 1996, COMPREHENSIVE HETERO, V5, P37

[5] Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A [J].

Comins, DL ;

Huang, SL ;

McArdle, CL ;

Ingalls, CL .

ORGANIC LETTERS, 2001, 3 (03) :469-471

[6] EFFICIENT SYNTHESIS AND RESOLUTION OF TRANS-2-(1-ARYL-1-METHYLETHYL)CYCLOHEXANOLS - PRACTICAL ALTERNATIVES TO 8-PHENYLMENTHOL [J].

COMINS, DL ;

SALVADOR, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4656-4661

[7] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].

COMINS, DL ;

JOSEPH, SP ;

GOEHRING, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4719-4728

[8] Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts [J].

Comins, DL ;

Kuethe, JT ;

Hong, H ;

Lakner, FJ ;

Concolino, TE ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2651-2652

[9] C-3 acetoxylation of N-acyl-2,3-dihydro-4-pyridones [J].

Comins, DL ;

Stolze, DA ;

Thakker, P ;

McArdle, CL .

TETRAHEDRON LETTERS, 1998, 39 (32) :5693-5696

[10] THE 1ST ENANTIOSELECTIVE TOTAL SYNTHESES OF THE ALLOPUMILIOTOXIN-A ALKALOID-267A AND ALKALOID-339B [J].

GOLDSTEIN, SW ;

OVERMAN, LE ;

RABINOWITZ, MH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1179-1190

← 1 2 →