Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine

被引：21
作者：
Bennasar, M-Lluisa [1 ]
Zulaica, Ester
Sole, Daniel
Alonso, Sandra
机构：
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
来源：
TETRAHEDRON | 2012年 / 68卷 / 24期
关键词：
Alkaloids; Ervitsine; Ring-closing metathesis; Heck cyclization; SYNTHETIC APPLICATIONS; INDOLE ALKALOIDS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; STRYCHNOS ALKALOIDS; OLEFIN METATHESIS; CONCISE SYNTHESIS; PALLADIUM; INTERMEDIATE; HETEROCYCLES;
D O I：
10.1016/j.tet.2012.04.022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chemoselective indole-templated ring-closing metathesis is used to assemble the cyclohepta[b]indole substructure of the indole alkaloid ervitsine. A subsequent intramolecular Heck coupling of the resulting alkene functionality with an amino-tethered vinyl halide accomplishes the closure of the unique 2-azabicyclo[4.3.1]decane framework of the alkaloid with concomitant incorporation of the exocyclic E-ethylidene substituent. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4641 / 4648
页数：8
相关论文
共 53 条
  • [1] Conjugate Addition of 2-Acetylindole Enolates to Unsaturated Oxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic Ring System of Ervitsine
    Amat, Mercedes
    Checa, Begona
    Llor, Nuria
    Perez, Maria
    Bosch, Joan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 898 - 907
  • [2] ANDRIANTSIFERANA M, 1977, TETRAHEDRON LETT, P2587
  • [3] Bachman G.B., 1933, Journal of the American Chemical Society, V55, P4279
  • [4] A SYNTHETIC ROAD TO THE FOREST OF STRYCHNOS, ASPIDOSPERMA, SCHIZOZYGANE AND EBURNAMINE ALKALOIDS BY WAY OF THE NOVEL PHOTO-ISOMERIZATION
    BAN, Y
    YOSHIDA, K
    GOTO, J
    OISHI, T
    TAKEDA, E
    [J]. TETRAHEDRON, 1983, 39 (22) : 3657 - 3668
  • [5] Rapid synthesis of the ervitsine alkaloid skeleton by a sequential RCM-Heck cyclization approach
    Bennasar, M. -Lluisa
    Zulaica, Ester
    Sole, Daniel
    Alonso, Sandra
    [J]. SYNLETT, 2008, (05) : 667 - 670
  • [6] Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
    Bennasar, M. -Lluisa
    Zulaica, Ester
    Sole, Daniel
    Alonso, Sandra
    [J]. TETRAHEDRON, 2007, 63 (04) : 861 - 866
  • [7] A Straightforward Synthetic Entry to Cleavamine-Type Indole Alkaloids by a Ring-Closing Metathesis-Vinyl Halide Heck Cyclization Strategy
    Bennasar, M. -Lluisa
    Sole, Daniel
    Zulaica, Ester
    Alonso, Sandra
    [J]. ORGANIC LETTERS, 2011, 13 (08) : 2042 - 2045
  • [8] Total Synthesis of the Bridged Indole Alkaloid Apparicine
    Bennasar, M. -Lluisa
    Zulaica, Ester
    Sole, Daniel
    Roca, Tomas
    Garcia-Diaz, Davinia
    Alonso, Sandra
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) : 8359 - 8368
  • [9] The first total synthesis of (±)-apparicine
    Bennasar, M. -Lluisa
    Zulaica, Ester
    Sole, Daniel
    Alonso, Sandra
    [J]. CHEMICAL COMMUNICATIONS, 2009, (23) : 3372 - 3374
  • [10] Bennasar ML, 2003, TETRAHEDRON-ASYMMETR, V14, P469, DOI 10.1016/S0924-2244(03)00154-7
123456