Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones.: First total synthesis of both enantiomers of pipermethystine

被引:33
|
作者
Arrayás, RG [1 ]
Alcudia, A [1 ]
Liebeskind, LS [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
关键词
D O I
10.1021/ol010183+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(lh)-pyridones using a ring closing metathesis and a lipase-mediated kinetic resolution as key steps is described and applied to the first synthesis of both enantiomers of pipermethystine.
引用
收藏
页码:3381 / 3383
页数:3
相关论文
共 50 条
  • [1] Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones
    Casamitjana, N
    López, V
    Jorge, A
    Bosch, J
    Molins, F
    Roig, A
    TETRAHEDRON, 2000, 56 (24) : 4027 - 4042
  • [2] A facile synthesis of 5,6-dihydro-5-hydroxy-2(1H)-pyridone
    Upadhyay, Puspesh K.
    Prasad, Rajendra
    Pandey, Menaka
    Kumar, Pradeep
    TETRAHEDRON LETTERS, 2009, 50 (20) : 2440 - 2442
  • [3] Diels-Alder reactions of 5,6-dihydro-2(1H)-pyridones. Preparation of partially reduced cis-isoquinolones and cis-3,4-disubstituted piperidines
    Casamitjana, N
    Jorge, A
    Perez, CG
    Bosch, J
    Espinosa, E
    Molins, E
    TETRAHEDRON LETTERS, 1997, 38 (13) : 2295 - 2298
  • [4] STEREOSELECTIVE SYNTHESES OF SUBSTITUTED 5,6-DIHYDRO-2(1H)-PYRIDINONES IN POLYPHOSPHATE MEDIA
    MARSON, CM
    GRABOWSKA, U
    FALLAH, A
    WALSGROVE, T
    EGGLESTON, DS
    BAURES, PW
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02): : 291 - 296
  • [5] 4-HYDROXY-6,6-DIMETHYL-5,6-DIHYDRO-2(1H)-PYRIDINETHIONE AND ONE AND THE CORRESPONDING TAUTOMERS
    ZIGEUNER, G
    SCHWEIGER, K
    FUCHSGRUBER, A
    MONATSHEFTE FUR CHEMIE, 1981, 112 (02): : 187 - 197
  • [6] NOVEL-APPROACH TO THE SYNTHESIS OF 6-SUBSTITUTED 5,6-DIHYDRO-2(2H)-PYRANONES
    FEHR, C
    GALINDO, J
    OHLOFF, G
    HELVETICA CHIMICA ACTA, 1981, 64 (05) : 1247 - 1256
  • [7] A NOVEL AND FACILE 2 STEP SYNTHESIS OF 5-ARYL-2(1H)-PYRIDONES
    SINGH, B
    SYNTHESIS-STUTTGART, 1985, (03): : 305 - 306
  • [8] Preparation of 5,6-dihydro-2(1H)-pyridinones by an intramolecular wittig reaction using N-3-oxoalkylchloracetamides
    Fisyuk A.S.
    Poendaev N.V.
    Bundel' Yu.G.
    Chemistry of Heterocyclic Compounds, 1998, 34 (2) : 258 - 259
  • [9] DERIVATIVES OF 1,3-PYRIMIDINE-THIONE (5,6-DIHYDRO-2(1H)-PYRIMIDINETHIONE) AS ADDITIVES FOR SYNTHETIC LUBRICATING OILS
    BARABANOVA, GV
    KLIMOV, AK
    IVANOV, VI
    KOSSOVA, LV
    VILENCHUK, FS
    BEBIKH, GF
    CHEMISTRY AND TECHNOLOGY OF FUELS AND OILS, 1980, 16 (11-1) : 780 - 782
  • [10] STUDIES ON HETEROCYCLIC-COMPOUNDS .3. 4,6-DISUBSTITUTED 5,6-DIHYDRO-2(1H)PYRIMIDINETHIONES
    NAIK, SK
    BEHERA, RK
    NAYAK, A
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1982, 21 (12): : 1124 - 1125