A HIGHLY STEREOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CIS-ALPHA,BETA-DIBENZYL-GAMMA-BUTYROLACTONES

被引:11
|
作者
MORITANI, Y
FUKUSHIMA, C
OGIKU, T
UKITA, T
MIYAGISHIMA, T
IWASAKI, T
机构
[1] TANABE SEIYAKU CO LTD,DEPT SYNTHET CHEM,APPL BIOCHEM RES LAB,3-16-89 KASHIMA,YODOGAWA,OSAKA 532,JAPAN
[2] TANABE SEIYAKU CO LTD,DIV R&D LOGIST,TODA,SAITAMA 335,JAPAN
关键词
D O I
10.1016/S0040-4039(00)73562-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alpha-Substituted cis-alpha, beta-dibenzyl-gamma-butyrolactones (1) were synthesized in good yields in a highly diastereoselective manner via electrophilic additions to the metal enolates of beta, gamma-disubstituted alpha-benzyl-gamma-butyrolactones (2) as a key step.
引用
收藏
页码:2787 / 2790
页数:4
相关论文
共 50 条
  • [1] A SYNTHESIS OF ALPHA-SUBSTITUTED TRANS-ALPHA,BETA-DIBENZYL-GAMMA-BUTYROLACTONES - DIASTEREOFACIAL DIFFERENTIATION IN THE ELECTROPHILIC ATTACK ON THE METAL ENOLATES OF ALPHA,BETA-DIBENZYL-GAMMA-BUTYROLACTONES
    MORITANI, Y
    UKITA, T
    NISHITANI, T
    SEKI, M
    IWASAKI, T
    TETRAHEDRON LETTERS, 1990, 31 (25) : 3615 - 3618
  • [2] THE FIRST SYNTHESIS OF (+/-)-CYCLOOLIVIL - A HIGHLY STEREOSELECTIVE SYNTHESIS OF 3-HYDROXY-1-ARYLTETRALIN LIGNANS BASED ON THE STEREOSELECTIVE HYDROXYLATION OF ALPHA,BETA-DIBENZYL-GAMMA-BUTYROLACTONES
    MORITANI, Y
    UKITA, T
    OHMIZU, H
    IWASAKI, T
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (06) : 671 - 672
  • [3] STEREOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED ALPHA,BETA-UNSATURATED ESTERS
    HOUSE, HO
    RASMUSSON, GH
    JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11): : 4278 - &
  • [4] ANTICONVULSANT PROPERTIES OF ALPHA-SUBSTITUTED, GAMMA-SUBSTITUTED, AND ALPHA,GAMMA-SUBSTITUTED GAMMA-BUTYROLACTONES
    KLUNK, WE
    COVEY, DF
    FERRENDELLI, JA
    MOLECULAR PHARMACOLOGY, 1982, 22 (02) : 438 - 443
  • [5] New reagents for the stereoselective synthesis of cis-alpha,beta-unsaturated carboxylates and nitriles
    Zhang, TY
    OToole, JC
    Dunigan, JM
    Stewart, V
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 526 - ORGN
  • [6] STEREOSELECTIVE SYNTHESIS OF CIS-ALPHA, BETA-EPOXYKETONES VIA DIVALENT TIN ENOLATE
    MUKAIYAMA, T
    HAGA, T
    IWASAWA, N
    CHEMISTRY LETTERS, 1982, (10) : 1601 - 1604
  • [7] STEREOSELECTIVE SYNTHESIS OF BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-GAMMA-BUTYROLACTONES ON PYRANOSE TEMPLATES
    ALABED, Y
    ALTEL, TH
    VOELTER, W
    TETRAHEDRON, 1993, 49 (41) : 9295 - 9306
  • [8] ALPHA-SUBSTITUTED GAMMA-BUTYROLACTONES - NEW CLASS OF ANTICONVULSANT DRUGS
    KLUNK, WE
    MCKEON, AC
    COVEY, DF
    FERRENDELLI, JA
    SCIENCE, 1982, 217 (4564) : 1040 - 1042
  • [9] STEREOSELECTIVE REDUCTION OF ALPHA-SUBSTITUTED ALPHA-SUBSTITUTED BETA-KETO-ESTERS BY HYDROSTANNANE ORGANOTIN TRIFLATE
    SATO, T
    OTERA, J
    APPLIED ORGANOMETALLIC CHEMISTRY, 1994, 8 (04) : 431 - 432
  • [10] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED GAMMA-BUTYROLACTONES FROM GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED PHENYL SULFONES
    ROJO, J
    GARCIA, M
    CARRETERO, JC
    TETRAHEDRON, 1993, 49 (43) : 9787 - 9800