The asymmetric synthesis of D-galactose via an iterative syn-glycolate aldol strategy

被引：39

作者：

Davies, SG ^{[1
]}

Nicholson, RL ^{[1
]}

Smith, AD ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

SYNLETT | 2002年 / 10期

关键词：

asymmetric synthesis; monosaccharides; iterative glycolate aldol reaction; D-galactose;

D O I：

10.1055/s-2002-34215

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of D-galactose has been completed in eight steps and in > 14% yield from simple starting materials via an iterative syn-glycolate aldol strategy.

引用

页码：1637 / 1640

页数：4

共 50 条

[21] ASYMMETRIC-SYNTHESIS OF THE BENZOQUINOID ANSAMYCIN ANTITUMOR ANTIBIOTICS - TOTAL SYNTHESIS OF (+)-MACBECIN [J].

EVANS, DA ;

MILLER, SJ ;

ENNIS, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :471-485

[22] Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics [J].

Gijsen, HJM ;

Qiao, L ;

Fitz, W ;

Wong, CH .

CHEMICAL REVIEWS, 1996, 96 (01) :443-473

[23] THE SYNTHESIS OF A C-1-C-8 LACTONE FRAGMENT OF DISCODERMOLIDE [J].

GOLEC, JMC ;

JONES, SD .

TETRAHEDRON LETTERS, 1993, 34 (50) :8159-8162

[24] Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions [J].

Harris, JM ;

Keränen, MD ;

Nguyen, H ;

Young, VG ;

O'Doherty, GA .

CARBOHYDRATE RESEARCH, 2000, 328 (01) :17-36

[25] SYNTHESIS OF CARBOHYDRATES VIA TANDEM USE OF THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION AND ENZYME-CATALYZED ALDOL ADDITION-REACTIONS [J].

HENDERSON, I ;

SHARPLESS, KB ;

WONG, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :558-561

[26] Biocatalytic syntheses of protected D-mannose-d(5), D-mannose-d(7), D-mannitol-2,3,4,5,6-d(5), and D-mannitol-1,1,2,3,4,5,6,6-d(8) [J].

Hudlicky, T ;

Pitzer, KK ;

Stabile, MR ;

Thorpe, AJ ;

Whited, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :4151-4153

[27] Precursor directed biosynthesis of novel 6-deoxyerythronolide B analogs containing non-natural oxygen substituents and reactive functionalities [J].

Hunziker, D ;

Wu, N ;

Kenoshita, K ;

Cane, DE ;

Khosla, C .

TETRAHEDRON LETTERS, 1999, 40 (04) :635-638

[28] PARTIAL REDUCTION OF CARBOXYLIC-ACIDS TO ALDEHYDES VIA 3-ACYLTHIAZOLIDINE-2-THIONES WITH DIISOBUTYLALUMINUM HYDRIDE [J].

IZAWA, T ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1977, (12) :1443-1446

[29] PARTIAL REDUCTION OF CARBOXYLIC-ACIDS TO ALDEHYDES VIA 3-ACYLTHIAZOLIDINE-2-THIONES WITH DIISOBUTYLALUMINUM HYDRIDE AND WITH LITHIUM TRI-TERT-BUTOXYALUMINUM HYDRIDE [J].

IZAWA, T ;

MUKAIYAMA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (02) :555-558

[30] ENZYMATIC ASYMMETRIZATION IN ORGANIC MEDIA - SYNTHESIS OF UNNATURAL GLUCOSE FROM CYCLOHEPTATRIENE [J].

JOHNSON, CR ;

GOLEBIOWSKI, A ;

STEENSMA, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9414-9418

← 1 2 3 4 5 →