Model studies toward the total synthesis of the Lycopodium alkaloid spirolucidine

被引:15
作者
Comins, DL [1 ]
Williams, AL [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
关键词
D O I
10.1021/ol016556o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS A strategy for the synthesis of the spirocyclic core of spirolucidine was explored through a model study. The diene 4a was prepared and photolyzed to give the desired [2 + 2] photoadduct 17 containing the correct relative stereochemistry corresponding to spirolucidine.
引用
收藏
页码:3217 / 3220
页数:4
相关论文
共 35 条
  • [1] CONVERSION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES TO 4-CHLORO-1,2-DIHYDROPYRIDINES USING THE VILSMEIER REAGENT - SYNTHESIS OF (-)-CONIINE AND (PLUS-OR-MINUS)-LUPININE
    ALAWAR, RS
    JOSEPH, SP
    COMINS, DL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) : 7732 - 7739
  • [2] [Anonymous], 1996, Adv. Nitrogen Heterocycl
  • [3] SPIROLUCIDINE, A NEW LYCOPODIUM ALKALOID
    AYER, WA
    BALL, LF
    BROWNE, LM
    TORI, M
    DELBAERE, LTJ
    SILVERBERG, A
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02): : 298 - 302
  • [4] BOYLE P, 1967, P INT S DRUG RES, P206
  • [5] A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth Gilbert reagent)
    Brown, DG
    Velthuisen, EJ
    Commerford, JR
    Brisbois, RG
    Hoye, TR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2540 - 2541
  • [6] Comins D.L., 1996, COMPREHENSIVE HETERO, V5, P37
  • [7] SYNTHESIS AND SYNTHETIC UTILITY OF 1-ACYL-5-(TRIALKYLSILYL)-1,2-DIHYDROPYRIDINES - SYNTHESIS OF (+/-)-ELAEOKANINE-A
    COMINS, DL
    MYOUNG, YC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 292 - 298
  • [8] Photochemical reactions of chiral 2,3-dihydro-4(1H)-pyridones:: asymmetric synthesis of (-)-perhydrohistrionicotoxin
    Comins, DL
    Zhang, YM
    Zheng, XL
    [J]. CHEMICAL COMMUNICATIONS, 1998, (22) : 2509 - 2510
  • [9] A NOVEL-APPROACH TO THE PERHYDROHISTRIONICOTOXIN RING-SYSTEM
    COMINS, DL
    ZHENG, XL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) : 2681 - 2682
  • [10] Anionic cyclizations of chiral 2,3-dihydro-4-pyridones: A five-step, asymmetric synthesis of indolizidine 209D
    Comins, DL
    Zhang, YM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (48) : 12248 - 12249