A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-EPIBATIDINE

被引:118
作者
CLAYTON, SC [1 ]
REGAN, AC [1 ]
机构
[1] UNIV MANCHESTER,DEPT CHEM,OXFORD RD,MANCHESTER M13 9PL,LANCS,ENGLAND
关键词
EPIBATIDINE; ANALGESIC; ALKALOID; PALLADIUM-CATALYZED COUPLING;
D O I
10.1016/S0040-4039(00)60162-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total synthesis of the potent non-opiate analgesic alkaloid epibatidine is described, in which the key step is a reductive palladium-catalysed Heck-type coupling. The synthesis is concise (two steps from known compounds), highly convergent, and completely stereoselective for the desired exo-isomer.
引用
收藏
页码:7493 / 7496
页数:4
相关论文
共 13 条
  • [1] ADDITION REACTIONS OF HETEROCYCLIC COMPOUNDS .8. METHYL PYRROLE-1-CARBOXYLATE AND DIMETHYL ACETYLENEDICARBOXYLATE
    ACHESON, RM
    VERNON, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JAN): : 457 - &
  • [2] SYNTHESES AND PHOTOELECTRON-SPECTRA OF 7-AZANORBORNADIENE AND RELATED-COMPOUNDS - AN ANALYSIS WITH FRAGMENT ORBITALS
    ALTENBACH, HJ
    CONSTANT, D
    MARTIN, HD
    MAYER, B
    MULLER, M
    VOGEL, E
    [J]. CHEMISCHE BERICHTE, 1991, 124 (04) : 791 - 801
  • [3] PALLADIUM-CATALYZED PREPARATION OF EXO-ARYL DERIVATIVES OF THE NORBORNANE SKELETON
    ARCADI, A
    MARINELLI, F
    BERNOCCHI, E
    CACCHI, S
    ORTAR, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 368 (02) : 249 - 256
  • [4] TOTAL SYNTHESIS OF EPIBATIDINE
    BROKA, CA
    [J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3251 - 3254
  • [5] THE SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE
    FLETCHER, SR
    BAKER, R
    CHAMBERS, MS
    HOBBS, SC
    MITCHELL, PJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) : 1216 - 1218
  • [6] PREPARATION AND PROPERTIES OF PYRIDINE-ANALOGUE OF TCNQ DIANION SALT
    HAMA, Y
    NOBUHARA, Y
    ASO, Y
    OTSUBO, T
    OGURA, F
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (05) : 1683 - 1686
  • [7] A VERSATILE TOTAL SYNTHESIS OF EPIBATIDINE AND ANALOGS
    HUANG, DF
    SHEN, TY
    [J]. TETRAHEDRON LETTERS, 1993, 34 (28) : 4477 - 4480
  • [8] PALLADIUM-CATALYZED INTERMOLECULAR ARYLATION AND ALKENYLATION OF BICYCLIC ALKENES
    LAROCK, RC
    JOHNSON, PL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) : 1368 - 1370
  • [9] MAGIDSON O, 1925, CHEM BER, V58, P113
  • [10] MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS
    MOHAMADI, F
    RICHARDS, NGJ
    GUIDA, WC
    LISKAMP, R
    LIPTON, M
    CAUFIELD, C
    CHANG, G
    HENDRICKSON, T
    STILL, WC
    [J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) : 440 - 467