Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine

被引：11
|
作者：
Yang, Lijuan [2 ,3 ]
Wang, Xuequan [1 ]
Pan, Zhiqiang [1 ]
Zhou, Ming [1 ]
Chen, Wen [2 ,3 ]
Yang, Xiaodong [1 ]
机构：
[1] Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China
[2] Yunnan Univ Nationalities, Key Lab Ethn Med Resource Chem, State Ethn Affairs Commiss, Kunming 650031, Yunnan, Peoples R China
[3] Minist Educ, Kunming 650031, Yunnan, Peoples R China
来源：
SYNLETT | 2011年 / 02期
基金：
中国国家自然科学基金;
关键词：
Amaryllidaceae alkaloids; crinine; oxocrinine; total synthesis; quaternary carbon; AZA-COPE REARRANGEMENTS; CONCISE TOTAL-SYNTHESIS; DIELS-ALDER REACTION; SCELETIUM ALKALOIDS; ANTIMALARIAL ACTIVITY; LYCORINE;
D O I：
10.1055/s-0030-1259288
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A flexible strategy leading to the synthesis of crinine-type Amaryllidaceae alkaloids, (+/-)-oxocrinine and (+/-)-crinine, has been developed. A notable feature in this synthetic route is the construction of tetrahydro-1H-benzo[c]azepine framework using an intramolecular Heck reaction and the formation of the sterically congested spiro cyclohexenone intermediate with a Robinson annulation.
引用
收藏
页码：207 / 210
页数：4
相关论文
共 50 条
  • [41] SYNTHETIC STUDIES TOWARDS THE TOTAL SYNTHESIS OF SAFRAMYCINS
    FUKUYAMA, T
    AJECK, KL
    SACHLEBEN, RA
    YANG, LH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 113 - ORGN
  • [42] Synthetic studies towards the total synthesis of taumycin
    deGruyter, Justine N.
    Maio, William
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [43] Synthetic studies towards the total synthesis of providencin
    Schweizer, Eliane
    Gaich, Tanja
    Brecker, Lothar
    Mulzer, Johann
    SYNTHESIS-STUTTGART, 2007, (24): : 3807 - 3814
  • [44] Studies towards the synthesis of guanidine alkaloids; Synthesis of a tricyclic guanidine from succinimide
    Louwrier, S
    Ostendorf, M
    Tuynman, A
    Hiemstra, H
    TETRAHEDRON LETTERS, 1996, 37 (06) : 905 - 908
  • [45] 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
  • [46] STUDIES IN SYNTHETIC PHOTOCHEMISTRY .1. SYNTHESIS OF NAPHTHAPHENANTHRIDINE ALKALOIDS
    KESSAR, SV
    SINGH, G
    BALAKRIS.P
    TETRAHEDRON LETTERS, 1974, (26) : 2269 - 2270
  • [47] SYNTHETIC STUDIES TOWARDS ANTI-LEUKEMIC ALKALOIDS .9. SYNTHESIS OF 15-ACETOXYDIHYDROCATHARANTHINE
    ATTAURRAHMAN
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1976, 31 (09): : 1303 - 1304
  • [48] Construction of the 5,10b-Phenanthridine Skeleton Using [3+2]-Cycloaddition of a Non-Stabilized Azomethine Ylide: Total Synthesis of (±)-Maritidine and (±)-Crinine Alkaloids
    Pandey, Ganesh
    Gupta, Nishant R.
    Gadre, Smita R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (04) : 740 - 750
  • [49] Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes
    Gomes, Jose
    Daeppen, Christophe
    Liffert, Raphael
    Roesslein, Joel
    Kaufmann, Elias
    Heikinheimo, Annakaisa
    Neuburger, Markus
    Gademann, Karl
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11017 - 11034
  • [50] Anionic Cyclization Approach toward Perhydroindoles: Total Synthesis of Montanine-Type Amaryllidaceae Alkaloids
    厦门大学学报(自然科学版), 1999, (S1) : 117 - 117
12345