Synthesis of indole-based propellane derivatives via Weiss-Cook condensation, Fischer indole cyclization, and ring-closing metathesis as key steps

被引:17
作者
Kotha, Sambasivarao [1 ]
Chinnam, Ajay Kumar [1 ]
Tiwari, Arti [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Powai, India
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷
关键词
allylation; indole derivatives; propellanes; ring-closing metathesis; Weiss-Cook condensation; IMINIUM ION CYCLIZATION; CONCISE TOTAL-SYNTHESIS; GENERAL-APPROACH; A-C; ALKALOIDS; (+/-)-MINFIENSINE; POLYQUINENES; CONSTRUCTION; MINFIENSINE; SERIES;
D O I
10.3762/bjoc.9.307
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of highly functionalized indole-based [n.3.3]propellane derivatives is described. The synthesis of the propellane derivatives involves a Weiss-Cook condensation, a Fischer indole cyclization, and a ring-closing metathesis as key steps.
引用
收藏
页码:2709 / 2714
页数:6
相关论文
共 55 条
  • [1] [Anonymous], TOP HETEROCYCL CHEM, DOI DOI 10.1007/978-3-642-15733-2
  • [2] ALKALOIDS OF KOPSIA-LAPIDILECTA
    AWANG, K
    SEVENET, T
    PAIS, M
    HADI, AHA
    [J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07): : 1134 - 1139
  • [3] BAN Y, 1975, TETRAHEDRON LETT, P727
  • [4] Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671
  • [5] Bertz S.H., 1986, Organic Syntheses, V64, P27
  • [6] BROWN KS, 1963, TETRAHEDRON LETT, P1731
  • [7] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [8] Total Synthesis of (+)-Fendleridine (Aspidoalbidine) and (+)-1-Acetylaspidoalbidine
    Campbell, Erica L.
    Zuhl, Andrea M.
    Liu, Christopher M.
    Boger, Dale L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 3009 - 3012
  • [9] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION
    COX, ED
    COOK, JM
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1797 - 1842
  • [10] GENERAL-APPROACH FOR THE SYNTHESIS OF POLYQUINENES .2. SYNTHESIS OF TETRACYCLO[5.5.1.04,13.010,13]TRIDECANE-2,5,8,11-TETRAENE
    DESHPANDE, MN
    JAWDOSIUK, M
    KUBIAK, G
    VENKATACHALAM, M
    WEISS, U
    COOK, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (16) : 4786 - 4788