Synthesis of tetrahydropyrans from sugar lactones

被引：34

作者：

Estevez, JC

Fairbanks, AJ

Fleet, GWJ

机构：

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

[2] CSIC, Unidade Asociada, Santiago De Compostela 15706, Spain

[3] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15706, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 44期

关键词：

D O I：

10.1016/S0040-4020(98)00837-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dehydration of both gamma- and delta- hexonolactones, either by intramolecular nucleophilic displacement of triflate leaving groups at C-2, or by Mitsunobu type displacement of the OH-6, provides access to bicyclic lactones which contain tetrahydropyran rings. Reduction or nucleophilic ring opening of these bicyclic lactones furnishes polyfunctionalised tetrahydropyrans in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：13591 / 13620

页数：30

相关论文

共 27 条

[1] SPECIFIC SYNTHESIS AND STEREOCHEMICAL ASSIGNMENT OF THE DIASTEREOMERIC 3,5-O-BENZYLIDENE-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE ISOMERS [J].

AKERFELDT, K ;

BARTLETT, PA .

CARBOHYDRATE RESEARCH, 1986, 158 :137-145

[2] USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS [J].

ALVAREZ, E ;

CANDENAS, ML ;

PEREZ, R ;

RAVELO, JL ;

MARTIN, JD .

CHEMICAL REVIEWS, 1995, 95 (06) :1953-1980

[3] CHIRAL OXETANES FROM SUGAR LACTONES - SYNTHESIS OF DERIVATIVES OF 3,5-ANHYDRO-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCURONIC ACID AND OF 3,5-ANHYDRO-1,2-O-ISOPROPYLIDENE-BETA-L-IDURONIC ACID [J].

AUSTIN, GN ;

FLEET, GWJ ;

PEACH, JM ;

PROUT, K ;

SON, JC .

TETRAHEDRON LETTERS, 1987, 28 (40) :4741-4744

[4] Intramolecular Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double-bond geometry in controlling the diastereoselectivity of cyclizations leading to 2,6-disubstituted tetrahydropyrans and piperidines [J].

Banwell, MG ;

Bissett, BD ;

Bui, CT ;

Pham, HTT ;

Simpson, GW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (01) :9-18

[5] Stereocontrolled synthesis of cyclic ethers by intramolecular hetero-Michael addition .5. Synthesis of all diastereoisomers of 2,3,5,6-tetrasubstituted tetrahydropyrans [J].

Betancort, JM ;

Martin, VS ;

Padron, JM ;

Palazon, JM ;

Ramirez, MA ;

Soler, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4570-4583

[6] ACETONIDES OF ALPHA-HYDROXY-DELTA-ALTRONOLACTONES [J].

BICHARD, CJF ;

FAIRBANKS, AJ ;

FLEET, GWJ ;

RAMSDEN, NG ;

VOGT, K ;

DOHERTY, O ;

PEARCE, L ;

WATKIN, DJ .

TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :901-912

[7] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[8] THE RING CONTRACTION OF DELTA-LACTONES WITH LEAVING GROUP ALPHA-SUBSTITUENTS - A STRATEGY FOR THE SYNTHESIS OF 2,5-DISUBSTITUTED HIGHLY FUNCTIONALIZED HOMOCHIRAL TETRAHYDROFURANS [J].

CHOI, SMS ;

MYERSCOUGH, PM ;

FAIRBANKS, AJ ;

SKEAD, BM ;

BICHARD, CJF ;

MANTELL, SJ ;

SON, JC ;

FLEET, GWJ ;

SAUNDERS, J ;

BROWN, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (21) :1605-1607

[9]

Craig DC, 1997, SYNLETT, P1318

[10]

Defaye J., 1970, ADV CARBOHYD CHEM BI, V25, P181