STEREOSELECTIVE SYNTHESIS OF BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-GAMMA-BUTYROLACTONES ON PYRANOSE TEMPLATES

被引:25
|
作者
ALABED, Y [1 ]
ALTEL, TH [1 ]
VOELTER, W [1 ]
机构
[1] UNIV TUBINGEN,INST PHYSIOL CHEM,PHYS BIOCHEM ABT,HOPPE SEYLER STR 4,W-7400 TUBINGEN 1,GERMANY
关键词
D O I
10.1016/0040-4020(93)80016-M
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of sugar derived epoxy triflates 1 and 2 or epoxy ketoses 11 and 12 with ester or acid enolates followed by acid-catalyzed ring closure affords poly-substituted chiral butenolides in excellent yields.
引用
收藏
页码:9295 / 9306
页数:12
相关论文
共 50 条
  • [21] POTENTIAL ANTITUMOR AGENTS - SYNTHESIS OF BIFUNCTIONAL ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
    HOWIE, GA
    STAMOS, IK
    CASSADY, JM
    JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (02) : 309 - 313
  • [22] SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND (+)-MINTLACTONE
    CRISP, GT
    MEYER, AG
    TETRAHEDRON, 1995, 51 (20) : 5831 - 5846
  • [23] ALLERGENIC ALPHA-METHYLENE-GAMMA-BUTYROLACTONES - STUDY OF THE CAPACITY OF BETA-ACETOXY-HYDROXY-ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND BETA-HYDROXY-ALPHA-METHYLENE-GAMMA-BUTYROLACTONES TO INDUCE ALLERGIC CONTACT-DERMATITIS IN GUINEA-PIGS
    BARBIER, P
    BENEZRA, C
    JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (05) : 868 - 871
  • [24] SYNTHESIS OF BOC-CYS-ALA-OME AND ITS STEREOSELECTIVE ADDITION TO ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
    TALAGA, P
    SCHAEFFER, M
    MATTES, H
    BENEZRA, C
    STAMPF, JL
    TETRAHEDRON, 1989, 45 (16) : 5029 - 5038
  • [25] SYNTHETIC APPROACH TO SESQUITERPENOID ALPHA-METHYLENE-GAMMA-BUTYROLACTONES - DEOXYMULTIRADIATIN
    MARINO, JP
    BROWNE, LJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 36 - 36
  • [26] POTENTIAL ANTITUMOR AGENTS - SYNTHESIS AND TESTING OF BIFUNCTIONAL ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
    HOWIE, GA
    STAMOS, IK
    CASSADY, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1975, 170 (AUG24): : 40 - 40
  • [27] SYNTHESIS OF BETA-ALKYL-ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
    RODER, E
    KRAUSS, H
    LIEBIGS ANNALEN DER CHEMIE, 1992, (03): : 177 - 181
  • [28] A SYNTHESIS OF "BETA-METHYLENE-GAMMA-BUTYROLACTONES
    GREENE, AE
    COELHO, F
    DEPRES, JP
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11): : 1973 - 1975
  • [29] ALLENYL ETHERS AS PRECURSORS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND BOTRYODIPLODIN DERIVATIVES
    DULCERE, JP
    MIHOUBI, MN
    RODRIGUEZ, J
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21): : 5709 - 5716
  • [30] STEREOCHEMISTRY OF THE MICHAEL ADDITION OF LYSINE DERIVATIVES TO ALPHA-METHYLENE-GAMMA-BUTYROLACTONES
    TALAGA, P
    BENEZRA, C
    STAMPF, JL
    BIOORGANIC CHEMISTRY, 1990, 18 (02) : 199 - 206