An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (±)-pancracine

被引:21
|
作者
Banwell, MG [1 ]
Edwards, AJ [1 ]
Jolliffe, KA [1 ]
Kemmler, M [1 ]
机构
[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia
关键词
D O I
10.1039/b102252k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of beta- nitrostyrene 4 with cyclohexane-1,3-dione (5) in the presence of DBU affords the Michael-addition product 6, which is readily elaborated, using straightforward chemistry, to the 5,11-methanomorphanthridine 2, acquisition of which constitutes a formal total synthesis of the racemic modification of the montanine alkaloid pancracine (1).
引用
收藏
页码:1345 / 1348
页数:4
相关论文
共 21 条
  • [1] TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, (+/-)-MONTANINE, (+/-)-COCCININE, (+/-)-PANCRACINE, AND (+/-)-BRUNSVIGINE
    HOSHINO, O
    ISHIZAKI, M
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (03) : 207 - 216
  • [2] A 1ST TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, (+/-)-COCCININE, (+/-)-MONTANINE, AND (+/-)-PANCRACINE
    ISHIZAKI, M
    HOSHINO, O
    IITAKA, Y
    TETRAHEDRON LETTERS, 1991, 32 (48) : 7079 - 7082
  • [3] Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids
    Wang, Fang
    Xu, Xiaohan
    Yan, Yangtian
    Zhang, Jiayang
    Yang, Yang
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (03) : 668 - 672
  • [4] RADICAL-MEDIATED SYNTHESIS OF THE 5,11-METHANOMORPHANTHRIDINE RING-SYSTEM - FORMAL TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, (+/-)-MONTANINE, (+/-)-COCCININE AND (+/-)-PANCRACINE
    ISHIZAKI, M
    KURIHARA, K
    TANAZAWA, E
    HOSHINO, O
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01): : 101 - 110
  • [5] Bioinspired Total Synthesis of Montanine-Type Amaryllidaceae Alkaloids
    Bao, Xu
    Cao, Ye-Xing
    Chu, Wen-Dao
    Qu, Hu
    Du, Ji-Yuan
    Zhao, Xian-He
    Ma, Xiao-Yan
    Wang, Cheng-Tao
    Fan, Chun-An
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) : 14167 - 14172
  • [7] Anionic cyclization approach toward perhydroindoles.: Total synthesis of montanine-type Amaryllidaceae alkaloids
    Sha, CK
    Huang, SJ
    Huang, CM
    Hong, AW
    Jeng, TH
    PURE AND APPLIED CHEMISTRY, 2000, 72 (09) : 1773 - 1776
  • [8] An expedient route to montanine-type amaryllidaceae alkaloids: Total syntheses of (-)-brunsvigine and (-)-manthine
    Hong, An-Wei
    Cheng, Tsung-Hui
    Raghukumar, Vellingiri
    Sha, Chin-Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19): : 7580 - 7585
  • [9] Pancracine, a Montanine-Type Amaryllidaceae Alkaloid, Inhibits Proliferation of A549 Lung Adenocarcinoma Cells and Induces Apoptotic Cell Death in MOLT-4 Leukemic Cells
    Koutova, Darja
    Havelek, Radim
    Peterova, Eva
    Muthna, Darina
    Kralovec, Karel
    Breiterova, Katerina
    Cahlikova, Lucie
    Rezacova, Martina
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2021, 22 (13)
  • [10] A FULLY REGIOCONTROLLED SYNTHESIS OF DESACETAMIDOISOCOLCHICINE - FORMAL TOTAL SYNTHESIS OF COLCHICINE
    BANWELL, MG
    LAMBERT, JN
    GULBIS, JM
    MACKAY, MF
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (20) : 1450 - 1452