CONVENIENT CHEMICAL RESOLUTION OF A BICYCLIC HYDROXYLACTONE OF SYNTHETIC INTEREST

被引:18
作者
BURLINA, F [1 ]
CLIVIO, P [1 ]
FOURREY, JL [1 ]
RICHE, C [1 ]
THOMAS, M [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
CHEMICAL RESOLUTION; CONFIGURATION; CYCLOPENTENE; LACTONE SYNTHON;
D O I
10.1016/0040-4039(94)88268-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The readily available bicyclic lactone 1 was resolved by treatment with (S)-O-acetyllactyl chloride to give a separable pair of diastereoisomers (-)-3 and (-)-4 the respective configuration of which was deduced from X-ray crystallography performed on the bromo derivative (-)-5.
引用
收藏
页码:8151 / 8152
页数:2
相关论文
共 6 条
  • [1] TOTAL SYNTHESIS OF (+/-)-SESBANIMIDE-A AND (+/-)-SESBANIMIDE-B
    GRIECO, PA
    HENRY, KJ
    NUNES, JJ
    MATT, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) : 368 - 370
  • [2] HETERO-DIELS-ALDER REACTION IN WATER - SYNTHESIS OF ALPHA-HYDROXY-GAMMA-LACTONES
    LUBINEAU, A
    AUGE, J
    LUBIN, N
    [J]. TETRAHEDRON LETTERS, 1991, 32 (51) : 7529 - 7530
  • [3] CONVERSION OF (-)-4-HYDROXY-2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONE INTO THE ANTI-HIV AGENT CARBOVIR
    MACKEITH, RA
    MCCAGUE, R
    OLIVO, HF
    PALMER, CF
    ROBERTS, SM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03): : 313 - 314
  • [4] MACKEITH RA, 1993, TETRAHEDRON LETT, V34, P3785
  • [5] STEREOISOMERIC FLAVOR COMPOUNDS .14. (S)-O-ACETYLLACTYL CHLORIDE - A VERSATILE CHIRAL AUXILIARY IN STEREODIFFERENTIATION OF ENANTIOMERIC FLAVOR COMPONENTS
    MOSANDL, A
    GESSNER, M
    GUNTHER, C
    DEGER, W
    SINGER, G
    [J]. JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY & CHROMATOGRAPHY COMMUNICATIONS, 1987, 10 (02): : 67 - 70
  • [6] SYNTHESIS OF NUCLEOSIDES AND RELATED-COMPOUNDS .33. SYNTHESIS OF 9-(C-5-HYDROXY-C-4-HYDROXYMETHYLCYCLOPENT-2-EN-R-1-YL)-9H-ADENINE [(+/-)-EPINOR-BCA]
    TOYOTA, A
    KATAGIRI, N
    KANEKO, C
    [J]. HETEROCYCLES, 1994, 38 (01) : 27 - 30