Combinatorial chemistry. Use of an intramolecular ruthenium catalyzed olefin/alkyne metathesis reaction in tandem with a Diels-Alder cycloaddition reaction to construct functionalized hexahydroisoindoles.

被引:50
作者
Heerding, DA [1 ]
Takata, DT [1 ]
Kwon, C [1 ]
Huffman, WF [1 ]
Samanen, J [1 ]
机构
[1] SmithKline Beecham Pharmaceut, Dept Med Chem, Collegeville, PA 19426 USA
关键词
combinatorial chemistry; metathesis; Diels-Alder reactions;
D O I
10.1016/S0040-4039(98)01473-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We show here the first example of a ruthenium catalyzed ene-yne metathesis reaction in tandem with a Diels-Alder cycloaddition reaction to efficiently form highly substituted hexahydroisoindole ring systems on Wang resin. This approach was used to prepare a 4200 membered combinatorial library. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6815 / 6818
页数:4
相关论文
共 15 条
  • [1] Discovery of novel pyridinopolyamines with potent antimicrobial activity: Deconvolution of mixtures synthesized by solution-phase combinatorial chemistry
    An, HY
    Haly, BD
    Cook, PD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (05) : 706 - 716
  • [2] Solid-phase synthesis of proline analogs via a three component 1,3-dipolar cycloaddition
    Hamper, BC
    Dukesherer, DR
    South, MS
    [J]. TETRAHEDRON LETTERS, 1996, 37 (21) : 3671 - 3674
  • [3] CATALYTIC RING CLOSING METATHESIS OF DIENYNES - CONSTRUCTION OF FUSED BICYCLIC RINGS
    KIM, SH
    BOWDEN, N
    GRUBBS, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) : 10801 - 10802
  • [4] Catalytic ring closing metathesis of dienynes: Construction of fused bicyclic [nm0] rings
    Kim, SH
    Zuercher, WJ
    Bowden, NB
    Grubbs, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) : 1073 - 1081
  • [5] Total synthesis of (-)-stemoamide using ruthenium-catalyzed enyne metathesis reaction
    Kinoshita, A
    Mori, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8356 - 8357
  • [6] KINOSHITA A, 1994, SYNLETT, P1020
  • [7] MARX MA, 1997, J AM CHEM SOC, V119, P6135
  • [8] Designed epothilones: Combinatorial synthesis, tubulin assembly properties, and cytotoxic action against taxol-resistant tumor cells
    Nicolaou, KC
    Vourloumis, D
    Li, TH
    Pastor, J
    Winssinger, N
    He, Y
    Ninkovic, S
    Sarabia, F
    Vallberg, H
    Roschangar, F
    King, NP
    Finlay, MRV
    Giannakakou, P
    VerdierPinard, P
    Hamel, E
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (19) : 2097 - 2103
  • [9] Discovery of a novel, potent, and specific family of factor Xa inhibitors via combinatorial chemistry
    Ostrem, JA
    Al-Obeidi, F
    Safar, P
    Safarova, A
    Stringer, SK
    Patek, M
    Cross, MT
    Spoonamore, J
    LoCascio, JC
    Kasireddy, P
    Thorpe, DS
    Sepetov, N
    Lebl, M
    Wildgoose, P
    Strop, P
    [J]. BIOCHEMISTRY, 1998, 37 (04) : 1053 - 1059
  • [10] Use of halomethyl resins to immobilize amines: An efficient method for synthesis of sulfonamides and amides on a solid support
    Raju, B
    Kogan, TP
    [J]. TETRAHEDRON LETTERS, 1997, 38 (28) : 4965 - 4968