Stereoselective synthesis of the antifungal GM222712

被引：27

作者：

Bueno, JM

Coterón, JM

Chiara, JL

Fernández-Mayoralas, A

Fiandor, JM

Valle, N

机构：

[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[2] Glaxo Wellcome SA, PTM, E-28760 Madrid, Spain

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 22期

关键词：

antifungals; carbohydrates; radical and radical reactions; alkylation;

D O I：

10.1016/S0040-4039(00)00655-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and convergent synthesis of the antifungal agent GM222712 is described. The approach involves the preparation of the modified sugar moiety followed by its stereoselective anomeric O-alkylation with sordaricin triflate 19. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：4379 / 4382

页数：4

相关论文

共 12 条

[1]

CABTREE RH, 1986, J ORG CHEM, V51, P2655

[2] A METHOD FOR THE SELECTIVE OXIDATION OF 1,4-DIOLS TO LACTOLS [J].

COREY, EJ ;

PALANI, A .

TETRAHEDRON LETTERS, 1995, 36 (20) :3485-3488

[3] Stereocontrolled glycosylation of sordaricin in the presence of ammonium salts [J].

Coterón, JM ;

Chiara, JL ;

Fernández-Mayoralas, A ;

Fiandor, JM ;

Valle, N .

TETRAHEDRON LETTERS, 2000, 41 (22) :4373-4377

[4]

GOMEZ JRR, Patent No. 14326

[5] Applications of tin-containing intermediates to carbohydrate chemistry [J].

Grindley, TB .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 53, 1998, 53 :17-142

[6]

HERREROS E, 1997, 13 C ISHAM PARM IT

[7] SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS [J].

HOVEYDA, AH ;

EVANS, DA ;

FU, GC .

CHEMICAL REVIEWS, 1993, 93 (04) :1307-1370

[8]

KOREEDA M, 1995, SYNLETT, P90

[9] HYDROXY GROUP DIRECTED HYDROGENATION WITH RHODIUM AND IRIDIUM CATALYSTS - SYNTHESIS OF A PROTECTED CHIRAL CARBOCYCLIC ANALOG OF DAUNOSAMINE [J].

MACHADO, AS ;

OLESKER, A ;

CASTILLON, S ;

LUKACS, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (06) :330-332

[10] ANOMERIC-OXYGEN ACTIVATION FOR GLYCOSIDE SYNTHESIS - THE TRICHLOROACETIMIDATE METHOD [J].

SCHMIDT, RR ;

KINZY, W .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 50, 1994, 50 :21-123