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
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
  • [21] Synthetic Studies on Erythrina Alkaloids: Formal Total Synthesis of (+)-3-Demethoxyerythratidinone
    Moon, Jong Taik
    Jung, Jin Ah
    Ha, Sung Hoon
    Song, Sung Ho
    Park, Sung Jun
    Kim, Jungahn
    Choo, Dong Joon
    Lee, Yong Sup
    Lee, Jae Yeol
    SYNTHETIC COMMUNICATIONS, 2011, 41 (09) : 1282 - 1292
  • [22] A NEW SYNTHETIC APPROACH TO AMARYLLIDACEAE ALKALOIDS . APPLICATION TO SYNTHESIS OF MESEMBRINE MESEMBRININE
    CURPHEY, TJ
    KIM, HL
    TETRAHEDRON LETTERS, 1968, (12) : 1441 - &
  • [23] Synthetic studies towards novel tetracyclic Lycopodium alkaloids: A synthesis of deoxymagellaninone
    Mehta, G
    Reddy, MS
    Thomas, A
    TETRAHEDRON, 1998, 54 (27) : 7865 - 7882
  • [24] Synthesis of the tetracyclic skeleton of the galanthamine-type Amaryllidaceae alkaloids
    Herke, Klara
    Hazai, Laszlo
    Hudak, Mate Szabolcs
    Abraham, Janka
    Santa, Zsuzsanna
    Hada, Viktor
    Szantay, Csaba, Jr.
    Szantay, Csaba
    ARKIVOC, 2009, : 235 - 246
  • [25] 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
  • [26] 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
  • [27] The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly
    Hu, Nan
    White, Lorenzo V.
    Lan, Ping
    Banwell, Martin G.
    MOLECULES, 2021, 26 (03):
  • [28] APPROACHES TO BIOGENETIC-TYPE ASYMMETRIC SYNTHESIS OF SOME AMARYLLIDACEAE ALKALOIDS
    TOMIOKA, K
    SHIMIZU, K
    YAMADA, SI
    KOGA, K
    HETEROCYCLES, 1977, 6 (9-10) : 1752 - 1756
  • [29] SYNTHETIC STUDIES ON CEPHALOTAXUS ALKALOIDS - A SYNTHESIS OF (+-)-CEPHALOTAXINE
    IKEDA, M
    OKANO, M
    KOSAKA, K
    KIDO, M
    ISHIBASHI, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (02) : 276 - 281
  • [30] SYNTHETIC STUDIES ON THE NARCICLASINE ALKALOIDS - A SYNTHESIS OF (+/-)-LYCORICIDINE
    MARTIN, SF
    TSO, HH
    HETEROCYCLES, 1993, 35 (01) : 85 - 88