Studies toward the synthesis of Stemona alkaloids; A short synthesis of the tricyclic core of tuberostemonines

被引：43
|
作者：
Goldstein, DM [1 ]
Wipf, P [1 ]
机构：
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 06期
关键词：
D O I：
10.1016/0040-4039(95)02302-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The tricyclic hydroindole core system of the Stemona alkaloids was prepared in 9 steps from N-Aloc-tyramine. The synthesis features oxidation of tyramine with hypervalent iodine followed by intramolecular conjugate addition and Mitsunobu cyclization of an amino-alcohol as the key steps.
引用
收藏
页码：739 / 742
页数：4
相关论文
共 50 条
  • [31] Short Approach toward the Nonracemic A,B,E Tricyclic Core of Calyciphylline B-Type Alkaloids
    Boissarie, Patrick
    Belanger, Guillaume
    ORGANIC LETTERS, 2017, 19 (14) : 3739 - 3742
  • [32] Synthesis of the tricyclic core of manzamine A
    Pathak, Ravindra B.
    Dobson, Benjamin C.
    Ghosh, Nandita
    Ageel, Khalid A.
    Alshawish, Madeha R.
    Saruengkhanphasit, Rungroj
    Coldham, Iain
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) : 3331 - 3340
  • [33] Synthesis of a tricyclic core of rameswaralide
    Trost, Barry M.
    Nguyen, Hien M.
    Koradin, Christopher
    TETRAHEDRON LETTERS, 2010, 51 (48) : 6232 - 6235
  • [34] Synthesis of the tricyclic core of halichlorine
    Hayakawa, I
    Arimoto, H
    Uemura, D
    CHEMICAL COMMUNICATIONS, 2004, (10) : 1222 - 1223
  • [35] A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
    Tetrahedron Lett, 38 (6943):
  • [36] A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
    Black, GP
    Murphy, PJ
    Walshe, NDA
    TETRAHEDRON, 1998, 54 (32) : 9481 - 9488
  • [37] A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
    Black, GP
    Murphy, PJ
    Walshe, NDA
    Hibbs, DE
    Hursthouse, MB
    Malik, KMA
    TETRAHEDRON LETTERS, 1996, 37 (38) : 6943 - 6946
  • [38] STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF SECURINEGA ALKALOIDS
    HEATHCOCK, CH
    JENNINGS, RA
    VONGELDERN, TW
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20): : 3428 - 3431
  • [39] Studies toward enantioselective total synthesis of the securinega alkaloids
    Han, GH
    Folmer, JJ
    Weinreb, SM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 74 - ORGN
  • [40] STUDIES DIRECTED TOWARD THE ULTIMATE SYNTHESIS FOR ERGOT ALKALOIDS
    SOMEI, M
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1988, 108 (05): : 361 - 380
12345