Regioselective synthesis of bridged azabicyclic compounds using radical translocations/cyclisations of methyl 2-alkynyl-1-(o-iodobenzoyl)pyrrolidine-2-carboxylates: a formal total synthesis of (+/-)-epibatidine

被引：29
作者：
Ikeda, M
Kugo, Y
Kondo, Y
Yamazaki, T
Sato, T
机构：
[1] Kyoto Pharmaceutical University, Misasagi, Yamashina
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 22期
关键词：
D O I：
10.1039/a705226j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bu3SnH-mediated radical translocations/cyclisations of methyl 2-alkynyl-1-(o-iodobenzoyl)pyrrolidine-2-carboxylates have been examined, The 2-[3-(trimethylsilyl)prop-2-ynyl]-8,2-[4-(trimethylsilyl)but-3- ynyl]-14, and 2-[5-(trimethylsilyl)pent-4-ynyl]-pyrrolidine derivatives 18, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave, regioselectively, the 7-azabicyclo-[2,2,1]heptane 19, 8-azabicyclo[3.2.1]octane 23, and 9-azabicyclo[4.2.1]nonane 26, respectively, The method has been applied to a formal total synthesis of (+/-)-epibatidine.
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页码：3339 / 3344
页数：6
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共 39 条
  • [1] Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine
    Albertini, E
    Barco, A
    Benetti, S
    DeRisi, C
    Pollini, GP
    Zanirato, V
    [J]. TETRAHEDRON LETTERS, 1997, 38 (04) : 681 - 684
  • [2] TOTAL SYNTHESIS OF (+/-)-EPIBATIDINE
    ALBERTINI, E
    BARCO, A
    BENETTI, S
    DERISI, C
    POLLINI, GP
    ROMAGNOLI, R
    ZANIRATO, V
    [J]. TETRAHEDRON LETTERS, 1994, 35 (49) : 9297 - 9300
  • [3] [Anonymous], COMPREHENSIVE ORGANI
  • [4] Synthesis of (+/-)-epibatidine and its analogues
    Bai, DG
    Xu, R
    Chu, GH
    Zhu, XG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4600 - 4606
  • [5] TOTAL SYNTHESIS OF EPIBATIDINE
    BROKA, CA
    [J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3251 - 3254
  • [6] Chirospecific syntheses of conformationally constrained 7-azabicycloheptane amino acids by transannular alkylation
    Campbell, JA
    Rapoport, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) : 6313 - 6325
  • [7] Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]heptanes
    Chen, ZM
    Trudell, ML
    [J]. CHEMICAL REVIEWS, 1996, 96 (03) : 1179 - 1193
  • [8] A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-EPIBATIDINE
    CLAYTON, SC
    REGAN, AC
    [J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7493 - 7496
  • [9] DESIGN AND SYNTHESIS OF POTENTIAL DNA CROSS-LINKING REAGENTS BASED ON THE ANTHRAMYCIN CLASS OF MINOR GROOVE BINDING-COMPOUNDS
    CONFALONE, PN
    HUIE, EM
    KO, SS
    COLE, GM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) : 482 - 487
  • [10] STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-EPIBATIDINE AND (-)-EPIBATIDINE
    COREY, EJ
    LOH, TP
    ACHYUTHARAO, S
    DALEY, DC
    SARSHAR, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5600 - 5602
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