RING CONTRACTION OF 3-DEOXY-2-O-TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXY-GAMMA-LACTONES TO OXETANES

被引：21

作者：

WITTY, DR

FLEET, GWJ

CHOI, S

VOGT, K

WILSON, FX

WANG, Y

STORER, R

MYERS, PL

WALLIS, CJ

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND

[2] GLAXO GRP RES LTD,WARE SG12 0DP,HERTS,ENGLAND

[3] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)97209-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring contraction of α-triflates of 3-deoxy-1,4-lactones bearing hydrogen or alkyl substituents in the 3-position to methyl oxetane-2-carboxylates on treatment with potassium carbonate in methanol is described. © 1990.

引用

页码：6927 / 6930

页数：4

共 17 条

[1] SYNTHESIS OF 3 3-C-HYDROXYMETHYLPENTOSES WITH THE D-RIBO-CONFIGURATIONS, D-XYLO-CONFIGURATIONS AND L-LYXO-CONFIGURATIONS - IDENTIFICATION OF THE LATTER WITH A MONOSACCHARIDE ISOLATED FROM PHASE-I COXIELLA-BURNETII LIPOPOLYSACCHARIDE [J].

DAHLMAN, O ;

GAREGG, PJ ;

MAYER, H ;

SCHRAMEK, S .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (01) :15-20

[2] COMPLEX QUINUCLIDINES (1-AZABICYCLO[2.2.2]OCTANES) FROM SUGARS - SYNTHESIS OF (1-ALPHA,3-ALPHA,4-ALPHA,5-ALPHA)-QUINUCLIDINE-3,5-DIOL FROM D-GLUCOSE [J].

FLEET, GWJ ;

MATHEWS, CJ ;

SEIJAS, JA ;

TATO, MPV ;

BROWN, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1067-1068

[3]

FLEET GWJ, 1987, TETRAHEDRON LETT, V28, P4741

[4]

HAMBALEK R, 1990, TETRAHEDRON LETT, V31, P4691

[5]

HOSHINO H, 1987, J ANTIBIOT, V40, P1078

[6]

HUDSON CS, 1929, J AM CHEM SOC, V51, P2225

[7] STABILIZATION OF THE THROMBOXANE RING-SYSTEM BY ELECTRON-WITHDRAWING SUBSTITUENTS - MECHANISM AND REACTIVITY IN THE HYDROLYSIS OF ALKYL AND ARYL OXETANE ACETALS [J].

KIRBY, AJ ;

RYDER, H ;

MATASSA, V .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (05) :825-831

[8] SELECTIVE TRANSFORMATIONS OF SUGAR TOSYLHYDRAZONES TO DEOXY AND UNSATURATED SUGARS [J].

NAIR, V ;

SINHABABU, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (26) :5013-5017

[9] SYNTHETIC STUDIES ON NEW SUGAR OXETANOSE - SYNTHESIS OF D-ERYTHROOXETANOSE AND ITS REACTION WITH SILYLATED ADENINE DERIVATIVE [J].

NISHIYAMA, S ;

OHGIYA, T ;

YAMAMURA, S ;

KATO, K ;

NAGAI, M ;

TAKITA, T .

TETRAHEDRON LETTERS, 1990, 31 (05) :705-708

[10] EVALUATION OF 2 POSSIBLE TRANSITION-STATES IN INTRAMOLECULAR OXETANE OXOLANE RING FORMATION BASED ON AM1 CALCULATIONS [J].

NISHIYAMA, S ;

YAMAMURA, S ;

KATO, K ;

NAGAI, M ;

TAKITA, T ;

TERADA, Y .

TETRAHEDRON LETTERS, 1990, 31 (33) :4777-4780

← 1 2 →