Synthesis of carbasugars from aldonolactones. Part II. Preparation of polyhydroxy/aminocyclopentanes functionalised at all five ring carbons

被引：18

作者：

Johansen, SK ^{[1
]}

Lundt, I ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 24期

关键词：

D O I：

10.1039/a907008g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from (1R,5R,8 R)-8-acetoxy-2-oxabicyclo[3.3.0]oct-6-en-3-one 4 the syntheses of 5-deoxy-4a(R)-hydroxy-4a-carba-alpha-D-ribo-hexofuranose 17, 5-deoxy-4a(R)-hydroxy-4a-carba-alpha-D-lyxo-hexofuranose 21, 5-deoxy-4a(R)-hydroxy-4a-carba-alpha-D-xylo-hexofuranose 23 and 4a(R)-hydroxy-2-amino-2,5-dideoxy-4a(R)-hydroxy-4a-carba-alpha-D-arabino-hexofuranose 1 have been achieved. The methodology included OsO4-catalysed dihydroxylation as well as regioselective epoxide opening followed by calcium borohydride reduction of the lactone moiety.

引用

页码：3615 / 3622

页数：8

共 23 条

[1] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[2]

BERECIBAR A, 1998, CARBOHYDRATE MIMICS

[3]

Blaser A, 1999, HELV CHIM ACTA, V82, P760

[4] Synthesis of trehazolin from D-glucose [J].

Boiron, A ;

Zillig, P ;

Faber, D ;

Giese, B .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :5877-5882

[5] New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides [J].

Crimmins, MT .

TETRAHEDRON, 1998, 54 (32) :9229-9272

[6] SYNTHESIS OF CARBOCYCLIC AMINONUCLEOSIDES [J].

DALUGE, S ;

VINCE, R .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2311-2320

[7] SYNTHESIS OF 1S,2R,3S,4R,5R-METHYL[2,3,4-TRIHYDROXY-5-(HYDROXYMETHYL)CYCLOPENTYL]AMINE - A POTENT ALPHA-MANNOSIDASE INHIBITOR [J].

FARR, RA ;

PEET, NP ;

KANG, MS .

TETRAHEDRON LETTERS, 1990, 31 (49) :7109-7112

[8] ANHYDROUS TERT-BUTYL HYDROPEROXIDE IN TOLUENE - THE PREFERRED REAGENT FOR APPLICATIONS REQUIRING DRY TBHP [J].

HILL, JG ;

ROSSITER, BE ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3607-3608

[9] Highly functionalized cyclopentanes by radical cyclization of unsaturated bromolactones. 2. A facile synthesis of the first carbaaldohexofuranoses and their conversion to carbapentofuranoses [J].

Horneman, AM ;

Lundt, I .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1919-1928

[10]

HORNEMAN AM, 1995, SYNLETT, P918

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