Synthesis of (±)-oleocanthal via a tandem intramolecular Michael cyclization-HWE olefination

被引:26
|
作者
English, Brandon J. [1 ]
Williams, Robert M. [1 ,2 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA
基金
美国国家卫生研究院;
关键词
ALPHA PRODUCTION; IRIDOIDS; INHIBITION; POTENT;
D O I
10.1016/j.tetlet.2009.03.145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of racemic oleocanthal has been accomplished in 11 steps from 1,3 propanediol by a key tandem intramolecular Michael cyclization-Horner-Wadsworth-Emmons olefination. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2713 / 2715
页数:3
相关论文
共 50 条
  • [1] An electrochemical tandem Michael addition, azidation and intramolecular cyclization strategy for the synthesis of imidazole derivatives
    Zhou, Kai
    Xia, Shendan
    Liu, Yanming
    Chen, Zhiwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (39) : 7840 - 7844
  • [2] Stereoselective tandem, Michael-intramolecular cyclization approach to functionalized pyrroloisoindolones
    Reyes, A
    Regla, I
    Fragoso, MC
    Vallejo, LA
    Demare, P
    Jiménez-Vázquez, HA
    Ramírez, Y
    Juaristi, E
    Tamariz, J
    TETRAHEDRON, 1999, 55 (37) : 11187 - 11202
  • [3] Domino cascade ring annulation via intramolecular Michael cyclization
    Belmessieri, Dorine
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [4] Asymmetric Total Synthesis of (-)-Scabronine G via Intramolecular Double Michael Reaction and Prins Cyclization
    Kanoh, Naoki
    Sakanishi, Kohei
    Iimori, Emiko
    Nishimura, Ken'ichi
    Iwabuchi, Yoshiharu
    ORGANIC LETTERS, 2011, 13 (11) : 2864 - 2867
  • [5] Highly Enantioslective Synthesis of Multisubstituted Polyfunctional Dihydropyrrole via an Organocatalytic Tandem Michael/Cyclization Sequence
    Zhang, Gen
    Zhang, Yaohu
    Jiang, Xianxing
    Yan, Wenjin
    Wang, Rui
    ORGANIC LETTERS, 2011, 13 (15) : 3806 - 3809
  • [6] Novel synthesis of oxocine derivatives by Wittig olefination and intramolecular Heck reaction via 8-endo trig cyclization
    Majumdar, K. C.
    Chattopadhyay, B.
    Sinha, B.
    TETRAHEDRON LETTERS, 2008, 49 (08) : 1319 - 1322
  • [7] Novel Synthesis of Oxathiocine Derivatives by Wittig Olefination and Intramolecular Heck Reaction via an 8-endo-trig Cyclization
    Majumdar, Krishna C.
    Chattopadhyay, Buddhadeb
    Sinha, Biswajit
    SYNTHESIS-STUTTGART, 2008, (23): : 3857 - 3863
  • [8] Spiroisoxazoline synthesis via intramolecular cyclization/methylation
    Xu, Jianping
    Wang, Jun
    Ellis, Erick D.
    Hamme, Ashton T., II
    SYNTHESIS-STUTTGART, 2006, 22 (22): : 3815 - 3818
  • [9] SYNTHESIS OF LENNOXAMINE VIA THE INTRAMOLECULAR CYCLIZATION OF ALKYNYLAMIDE
    KOSEKI, Y
    NAGASAKA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (09) : 1604 - 1606
  • [10] Synthesis of Multisubstituted 2-Aminopyrroles/pyridines via Chemoselective Michael Addition/Intramolecular Cyclization Reaction
    Qi, Xueyu
    Xiang, Haoyue
    He, Qian
    Yang, Chunhao
    ORGANIC LETTERS, 2014, 16 (16) : 4186 - 4189