TOTAL SYNTHESIS OF THE INDOLE ALKALOID (+/-)-TACAMONINE

被引：18
|
作者：
LOUNASMAA, M
BELLE, DD
TOLVANEN, A
机构：
[1] Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 39期
关键词：
D O I：
10.1016/0040-4039(95)01419-I
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient method is described for the preparation of tacamonine (1) from the easily accessible ester 3. The method is based on the stereoselective synthesis of 20-epitacamonine (7), which is transformed to 1 using the Polonovski-Potier reaction.
引用
收藏
页码：7141 / 7144
页数：4
相关论文
共 50 条
  • [21] Total Synthesis of the Indole Alkaloid (±)- and (+)-Methyl N-Decarbomethoxychanofruticosinate
    Wei, Yi
    Zhao, Duo
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 12988 - 12991
  • [22] Enantiospecific total synthesis of the enantiomer of the indole alkaloid intermediate macroline
    Liu, XX
    Zhang, CC
    Liao, XB
    Cook, JM
    TETRAHEDRON LETTERS, 2002, 43 (41) : 7373 - 7377
  • [23] Enantioselective total synthesis of the indole alkaloid 16-episilicine
    Amat, Mercedes
    Checa, Begona
    Llor, Nuria
    Molins, Elies
    Bosch, Joan
    CHEMICAL COMMUNICATIONS, 2009, (20) : 2935 - 2937
  • [24] INDOLE ALKALOID SYNTHESIS
    WENKERT, E
    HETEROCYCLES, 1984, 21 : 325 - 329
  • [25] Total synthesis of enantiomer of indole alkaloid affinisine and approach to the total synthesis of alstophylline and macralstonine.
    Liu, XX
    Wang, T
    Ma, CR
    Xu, QG
    Cook, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U51 - U51
  • [26] The first total synthesis of (-)-mitragynine, an analgesic indole alkaloid in Mitragyna speciosa
    Takayama, H
    Maeda, M
    Ohbayashi, S
    Kitajima, M
    Sakai, S
    Aimi, N
    TETRAHEDRON LETTERS, 1995, 36 (51) : 9337 - 9340
  • [27] TOTAL SYNTHESIS OF (+/-)-DRAGMACIDIN - A CYTOTOXIC BIS(INDOLE)ALKALOID OF MARINE ORIGIN
    JIANG, B
    SMALLHEER, JM
    AMARALLY, C
    WUONOLA, MA
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22): : 6823 - 6827
  • [28] Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
    Kong, A.
    Mancheno, D. E.
    Boudet, N.
    Delgado, R.
    Andreansky, E. S.
    Blakey, S. B.
    CHEMICAL SCIENCE, 2017, 8 (01) : 697 - 700
  • [29] Isolation and asymmetric total synthesis of a new Mitragyna indole alkaloid, (-)-mitralactonine
    Takayama, H
    Kurihara, M
    Kitajima, M
    Said, IM
    Aimi, N
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06): : 1772 - 1773
  • [30] Total synthesis of tetracyclic indole alkaloid ht-13-B
    Zhang, Yilin
    Hubbard, Jeremiah W.
    Akhmedov, Novruz G.
    Petersen, Jeffrey L.
    Soederberg, Bjoern C. G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
12345