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
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 23期
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
  • [41] Synthesis of the benzophenone fragment of balanol via an intramolecular cyclization event
    Denieul, MP
    Laursen, B
    Hazell, R
    Skrydstrup, T
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19): : 6052 - 6060
  • [42] Formal Synthesis of Aspidospermidine via the Intramolecular Cascade Transannular Cyclization
    Huang, Jiu-Zhong
    Jie, Xiao-Ke
    Wei, Kun
    Zhang, Hongbin
    Wang, Min-Cai
    Yang, Yu-Rong
    SYNLETT, 2013, 24 (10) : 1303 - 1306
  • [43] SYNTHESIS OF UNSUBSTITUTED THIA CROWN ETHERS VIA INTRAMOLECULAR CYCLIZATION
    NAKATSUJI, Y
    WATANABE, Y
    OKAHARA, M
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (02) : 627 - 628
  • [44] Synthesis of indole by intramolecular cyclization via ruthenium vinylidene complexes
    Lin, Ying-Chih
    Chiang, Pei-Yun
    Liu, Yi-Hong
    Wang, Yu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [45] SYNTHESIS OF INDOLINES VIA A PHOTOCATALYTIC INTRAMOLECULAR REDUCTIVE CYCLIZATION REACTION
    Yamaguchi, Eiji
    Goto, Yumiko
    Itoh, Akichika
    HETEROCYCLES, 2020, 101 (01) : 177 - 185
  • [46] Total Synthesis of (-)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization
    Gujarati, Priyansh D.
    Reber, Keith P.
    SYNTHESIS-STUTTGART, 2022, 54 (05): : 1404 - 1412
  • [47] Multicomponent Synthesis of Isoindolinone Frameworks via RhIII-Catalysed in situ Directing Group-Assisted Tandem Oxidative Olefination/Michael Addition
    Wang, Liang
    Liu, Xi
    Liu, Jian-biao
    Shen, Jun
    Chen, Qun
    He, Ming-yang
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (07) : 765 - 769
  • [48] Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions
    Cichowicz, Nathan R.
    Kaplan, Will
    Khomutnyk, Yaroslav
    Bhattarai, Bijay
    Sun, Zhankui
    Nagorny, Pavel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (45) : 14341 - 14348
  • [49] SYNTHESIS OF A TETRACYCLIC AMINOBENZIMIDAZOLE DERIVATIVE VIA TANDEM CYCLIZATION OF TRIPHENYLGUANIDINE
    Akamatsu, Yuki
    Kamino, Shinichiro
    Sawada, Daisuke
    HETEROCYCLES, 2019, 99 (02) : 815 - 819
  • [50] Total synthesis of cruciferane via epoxidation/tandem cyclization sequence
    Ghosh, Suman Kr
    Nagarajan, Rajagopal
    RSC ADVANCES, 2014, 4 (108): : 63147 - 63149
12345