An approach to the narciclasine alkaloids via a quinone methide initiated cyclization reaction

被引:24
|
作者
Angle, SR
Wada, T
机构
[1] Department of Chemistry, University of California-Riverside, Riverside
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)10138-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective synthesis of a possible intermediate for the synthesis of the narciclasine alkaloids from D-glucose is described. The key step of the sequence is a quinone methide initiated cyclization reaction, (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7955 / 7958
页数:4
相关论文
共 50 条
  • [41] Intramolecular Condensation via an o-Quinone Methide: Total Synthesis of (±)-Heliol
    Green, Jason C.
    Brown, Eric R.
    Pettus, Thomas R. R.
    ORGANIC LETTERS, 2012, 14 (12) : 2929 - 2931
  • [42] SYNTHESIS OF SOME NEW TETRACYCLIC HETEROAROMATIC CHROMANS VIA QUINONE METHIDE INTERMEDIATES
    CHAUHAN, MS
    MCKINNON, DM
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (14): : 2223 - 2227
  • [43] SYNTHESIS OF A VARIETY OF POLYCYCLIC HETEROAROMATIC-COMPOUNDS VIA QUINONE METHIDE INTERMEDIATES
    ASHERSON, JL
    YOUNG, DW
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (24) : 916 - 917
  • [44] Radical-initiated cyclization as a key step for the synthesis of oxoprotoberberine alkaloids
    Lee, Chih-Shone
    Yu, Tsung-Ching
    Luo, Jian-Wen
    Cheng, Yen-Yao
    Chuang, Che-Ping
    TETRAHEDRON LETTERS, 2009, 50 (31) : 4558 - 4562
  • [45] DMAP catalyzed addition-cyclization reaction of 2-hydroxyphenyl-para-quinone methide with nitroalkenes: Facile entry into highly substituted chromane derivatives
    Maripally, Narsimulu
    Reddy, Venkatram R.
    Donthi, Ravikiran
    Mutyala, Raghupathi
    Chandra, Rajesh
    TETRAHEDRON LETTERS, 2020, 61 (09)
  • [46] Synthesis of chromans from the reaction of o-quinone methide precursor with substituted styrenes
    Bilgic, Sevim
    Bilgic, Orhan
    Bueyuekkidan, Buelent
    Guendueza, Murat
    JOURNAL OF CHEMICAL RESEARCH-S, 2007, (02): : 76 - 79
  • [47] Photogeneration of quinone methide from adamantylphenol in an ultrafast non-adiabatic dehydration reaction
    Forjan, Mateo
    Zgrablic, Goran
    Vdovic, Silvije
    Sekutor, Marina
    Basaric, Nikola
    Kabacinski, Piotr
    Pashaki, Maryam Nazari Haghighi
    Frey, Hans-Martin
    Cannizzo, Andrea
    Cerullo, Giulio
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2022, 24 (07) : 4384 - 4393
  • [48] Catalyst- free [4+2] cyclization of para- quinone methide derivatives with homophthalic anhydrides
    Zhou, Jia-Yu
    Ma, Chun
    Zhang, Yi-Zhu
    Wu, Qiong
    Shi, Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (48) : 9382 - 9389
  • [49] Metal-Catalyzed (4+3) Cyclization of Vinyl Aziridines with para-Quinone Methide Derivatives
    Jiang, Fei
    Yuan, Fu-Ru
    Jin, Li-Wen
    Mei, Guang-Jian
    Shi, Feng
    ACS CATALYSIS, 2018, 8 (11): : 10234 - 10240
  • [50] Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums
    Wu, Xingxing
    Sparr, Christof
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (19)