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

页码：13591 / 13620

页数：30

共 27 条

[21] OXIDATION OF 1,2-5,6-DI-O-ISOPROPYLIDENE-D-GLUCOSE BY DIMETHYL SULFOXIDE-ACETIC ANHYDRIDE [J].

SOWA, W ;

THOMAS, GHS .

CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (07) :836-&

[22]

Takagi R, 1997, HETEROCYCLES, V45, P2313

[23]

WEATLEY JR, 1993, J CHEM SOC CHEM COMM, P1065

[24]

Williams N.R., 1970, ADV CARBOHYD CHEM, V25, P109

[25] RING CONTRACTION OF 2-O-TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXY-GAMMA-LACTONES TO OXETANE CARBOXYLIC ESTERS [J].

WITTY, DR ;

FLEET, GWJ ;

VOGT, K ;

WILSON, FX ;

WANG, Y ;

STORER, R ;

MYERS, PL ;

WALLIS, CJ .

TETRAHEDRON LETTERS, 1990, 31 (33) :4787-4790

[26] RING CONTRACTION OF 3-DEOXY-2-O-TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXY-GAMMA-LACTONES TO OXETANES [J].

WITTY, DR ;

FLEET, GWJ ;

CHOI, S ;

VOGT, K ;

WILSON, FX ;

WANG, Y ;

STORER, R ;

MYERS, PL ;

WALLIS, CJ .

TETRAHEDRON LETTERS, 1990, 31 (47) :6927-6930

[27] THE TOTAL SYNTHESIS OF (-)-LITSENOLIDES C-1 AND C-2 [J].

WOOD, WW ;

WATSON, GM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2681-2688

← 1 2 3 →