SYNTHETIC APPLICATIONS OF 2-(1,3-DITHIAN-2-YL)INDOLES .3. A NEW ROUTE TO TETRACYCLIC [ABCD] INTERMEDIATES IN THE SYNTHESIS OF ASPIDOSPERMA INDOLE ALKALOIDS

被引：0
|
作者：
TROIN, Y [1 ]
DIEZ, A [1 ]
BETTIOL, JL [1 ]
RUBIRALTA, M [1 ]
GRIERSON, DS [1 ]
HUSSON, HP [1 ]
机构：
[1] CNRS,INST CHIM SUBST NAT,F-91190 GIF SUR YVETTE,FRANCE
来源：
HETEROCYCLES | 1991年 / 32卷 / 04期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of tetracyclic [ABCD] framework of Aspidosperma alkaloids has been achieved via allylamine-enamine isomerization using (Ph3P)3RhCl in hot aqueous acetonitrile of the 1,2,5,6-tetrahydro-3-(indolylethyl)-pyridine (13) which in turn was obtained by Raney nickel desulfurization of the corresponding 2-(1,3-dithian-2-yl)indole (5a).
引用
收藏
页码：663 / 668
页数：6
相关论文
共 50 条
  • [1] SYNTHETIC APPLICATIONS OF 2-(1,3-DITHIAN-2-YL)INDOLES - A NEW SYNTHETIC APPROACH TO STRYCHNOS ALKALOIDS
    RUBIRALTA, M
    TORRENS, A
    REIG, I
    GRIERSON, DS
    HUSSON, HP
    HETEROCYCLES, 1989, 29 (11) : 2121 - 2133
  • [2] SYNTHETIC APPLICATIONS OF 2-(1,3-DITHIAN-2-YL)INDOLES .4. NEW SYNTHESIS OF THE TETRACYCLIC ABED RING-SYSTEM OF STRYCHNOS ALKALOIDS
    DIEZ, A
    CASTELLS, J
    FORNS, P
    RUBIRALTA, M
    GRIERSON, DS
    HUSSON, HP
    SOLANS, X
    FONTBARDIA, M
    TETRAHEDRON, 1994, 50 (22) : 6585 - 6602
  • [3] Synthetic applications of 2-(1,3-dithian-2-yl)indoles .7. Synthesis of aspidospermidine
    Forns, P
    Diez, A
    Rubiralta, M
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22): : 7882 - 7888
  • [4] SYNTHETIC APPLICATIONS OF 2-(1,3-DITHIAN-2-YL)INDOLES .5. ASYMMETRIC-SYNTHESIS OF DASYCARPIDONE-TYPE INDOLE ALKALOIDS
    MICOUIN, L
    DIEZ, A
    CASTELLS, J
    LOPEZ, D
    RUBIRALTA, M
    QUIRION, JC
    HUSSON, HP
    TETRAHEDRON LETTERS, 1995, 36 (10) : 1693 - 1696
  • [5] Synthetic Applications of 2-(1,3-Dithian-2-yl)indoles. 7. Synthesis of Aspidospermidine
    J Org Chem, 22 (7882):
  • [6] Synthetic applications of 2-(1,3-dithian-2-yl)indoles .6. Synthesis of 20-epidasycarpidone
    Forns, P
    Diez, A
    Rubiralta, M
    Solans, X
    FontBardia, M
    TETRAHEDRON, 1996, 52 (10) : 3563 - 3574
  • [7] Synthetic Applications of 2-(1,3-Dithian-2-yl)indoles VI. Synthesis of 20-Epidasycarpidone
    Forns, P.
    Diez, A.
    Rubiralta, M.
    Tetrahedron, 52 (10):
  • [8] SYNTHESIS AND REACTIVITY OF 2-(1,3-DITHIAN-2-YL)INDOLES .3. INFLUENCE OF THE INDOLE PROTECTIVE N-PHENYLSULFONYL GROUP
    RUBIRALTA, M
    DIEZ, A
    REIG, I
    CASTELLS, J
    BETTIOL, JL
    GRIERSON, DS
    HUSSON, HP
    HETEROCYCLES, 1990, 31 (01) : 173 - 186
  • [9] SYNTHETIC APPLICATIONS OF 2-(1,3-DITHIAN-2-YL)INDOLES - SYNTHESIS OF 1-METHYL-15-HYDROXY-20-DEETHYLDASYCARPIDONE
    RUBIRALTA, M
    TORRENS, A
    PALET, A
    GRIERSON, DS
    HUSSON, HP
    TETRAHEDRON LETTERS, 1989, 30 (48) : 6761 - 6764
  • [10] SYNTHESIS AND REACTIVITY OF 2-(1,3-DITHIAN-2-YL) INDOLES .2. SYNTHESIS OF 2-ACYLINDOLE DERIVATIVES
    BENNASAR, ML
    TORRENS, A
    RUBIRALTA, M
    BOSCH, J
    GRIERSON, DS
    HUSSON, HP
    HETEROCYCLES, 1989, 29 (04) : 745 - 760
12345