A facile method for the solution and solid-phase synthesis of substituted [3.3.1] bicycles

被引:80
作者
Nicolaou, KC
Pfefferkorn, JA
Cao, GQ
Kim, S
Kessabi, J
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Biochem & Chem, La Jolla, CA 92093 USA
关键词
D O I
10.1021/ol990791d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Interest in bicyclic natural products from the Guttiferae classification has led to the development of an improved method for the selenium mediated cyclization of alkenyl-substituted beta-dicarbonyls (I) to form a variety of bicyclo[3.3.1]nonan-9-ones (II) both in solution and on solid support.
引用
收藏
页码:807 / 810
页数:4
相关论文
共 34 条
  • [1] Alves TMD, 1999, J NAT PROD, V62, P369, DOI 10.1021/np9803833
  • [2] ORGANIC-REACTIONS AT HIGH-PRESSURE - A ROBINSON ANNULATION SEQUENCE INITIATED BY MICHAEL ADDITION OF ACTIVATED CYCLOALKANONES WITH HINDERED ENONES
    DAUBEN, WG
    BUNCE, RA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) : 4642 - 4648
  • [3] Two polyisoprenylated benzophenones from the floral resins of three Clusia species
    de Oliveira, CMA
    Porto, ALM
    Bittrich, V
    Marsaioli, AJ
    [J]. PHYTOCHEMISTRY, 1999, 50 (06) : 1073 - 1079
  • [4] Floral resins of Clusia spp: Chemical composition and biological function
    deOliveira, CMA
    Porto, ALM
    Bittrich, V
    Vencato, I
    Marsaioli, AJ
    [J]. TETRAHEDRON LETTERS, 1996, 37 (36) : 6427 - 6430
  • [5] ON THE DIRECT FORMATION OF EPISULFONIUM IONS FROM ALKENES - AN APPLICATION TO THE SYNTHESIS OF HIGHER-ORDER CARBOCYCLES VIA EPISULFONIUM ION INITIATED POLYENE CYCLIZATIONS
    EDSTROM, ED
    LIVINGHOUSE, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) : 949 - 951
  • [6] SYNTHESIS OF STABLE ANALOGS OF TXA2
    EVANS, EH
    HEWSON, AT
    MARCH, LA
    NOWELL, IW
    WADSWORTH, AH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01): : 137 - 149
  • [7] INTRAMOLECULAR LEWIS ACID-CATALYZED ALKYLATIONS
    EVANS, EH
    HEWSON, AT
    WADSWORTH, AH
    [J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (03) : 243 - 247
  • [8] ENAMINE CHEMISTRY .8. REACTION OF ACRYLOYL CHLORIDE WITH DIENAMINES
    FIRRELL, NF
    HICKMOTT, PW
    HOPKINS, BJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (10): : 1477 - &
  • [9] BRIDGED AMINOTETRALINS AS NOVEL POTENT ANALGESIC SUBSTANCES
    FREED, ME
    POTOSKI, JR
    FREED, EH
    CONKLIN, GL
    MALIS, JL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (06) : 595 - 599
  • [10] Fukuyama Y, 1997, CHEM PHARM BULL, V45, P947