Synthesis of bisabolane sesquiterpenes: A Johnson-Claisen rearrangement approach

被引:7
|
作者
Du, Zhen Ting [1 ]
Yu, Hong Rui [1 ]
Xu, Yan [1 ]
Li, Yong [1 ]
Li, An Pai [2 ]
机构
[1] NW A&F Univ, Coll Sci, Yangling 712100, Peoples R China
[2] Synthet Technol Pte Ltd, Singapore 048693, Singapore
基金
中国国家自然科学基金;
关键词
Bisabolane sesquiterpenes; Johnson-Claisen rearrangement; Synthesis; ENANTIOSELECTIVE SYNTHESIS; ETHER; (+/-)-CURCUPHENOL; (+)-CURCUPHENOL; TERPENOIDS;
D O I
10.1016/j.cclet.2010.02.024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several bisabolane sesquiterpenes, (+/-)-curcumene, (+/-)-curcuphenol, (+/-)-curcudiol and (+/-)-curcuhydroquinone, have been synthesized in racemic form and fully characterized. The salient characteristic of our approach is that a Johnson-Claisen arrangement was involved as a key step. (C) 2010 Zhen Ting Du. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:813 / 815
页数:3
相关论文
共 50 条
  • [41] THE CLAISEN REARRANGEMENT APPROACH TO THE SYNTHESIS OF CALICHEAMICIN ESPERAMICIN AND NEOCARZINOSTATIN PRECURSORS AND ANALOGS
    MAGRIOTIS, PA
    KIM, KD
    SCOTT, ME
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 359 - ORGN
  • [42] The Tandem Claisen Rearrangement in Organic Synthesis
    Zhang, Xueqin
    Huang, Gangliang
    Huang, Siqi
    CURRENT ORGANIC CHEMISTRY, 2017, 21 (27) : 2776 - 2782
  • [43] CLAISEN AROMATIC REARRANGEMENT IN THE SYNTHESIS OF ELLIPTICINE
    MUSTAFIN, AG
    KHALILOV, IN
    ABDRAKHMANOV, IB
    TOLSTIKOV, GA
    KHIMIYA PRIRODNYKH SOEDINENII, 1989, (06): : 816 - 818
  • [44] An enantioselective epoxide rearrangement - Claisen rearrangement approach to prostaglandins and (+)-iridomyrmecin
    Hodgson, DM
    Gibbs, AR
    SYNLETT, 1997, (06) : 657 - 658
  • [45] Claisen-Johnson orthoester rearrangement of γ-hydroxy α,β-unsaturated ketones and nitriles
    Giardinà, A
    Marcantoni, E
    Mecozzi, T
    Petrini, M
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (04) : 713 - 718
  • [46] SYNTHESIS OF BRIDGED BICYCLOALKANES VIA THE ALICYCLIC CLAISEN REARRANGEMENT - A NEW APPROACH TO QUADRONE
    FUNK, RL
    ABELMAN, MM
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16): : 3247 - 3248
  • [47] Development of the Claisen Rearrangement/Organocatalytic Diels-Alder Approach for the Synthesis of Eunicellins
    Hooper, Joel F.
    White, Jonathan M.
    Holmes, Andrew B.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2014, 67 (8-9) : 1189 - 1194
  • [48] Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes
    Aggarwal, Varinder K.
    Ball, Liam T.
    Carobene, Simon
    Connelly, Rickki L.
    Hesse, Matthew J.
    Partridge, Benjamin M.
    Roth, Philippe
    Thomas, Stephen P.
    Webster, Matthew P.
    CHEMICAL COMMUNICATIONS, 2012, 48 (74) : 9230 - 9232
  • [49] SYNTHESIS OF ALLYL PHENYL ETHER AND CLAISEN REARRANGEMENT
    Torosyan, Gagik
    Hovhannisyan, Dezy
    SCIENTIFIC STUDY AND RESEARCH-CHEMISTRY AND CHEMICAL ENGINEERING BIOTECHNOLOGY FOOD INDUSTRY, 2011, 12 (04): : 425 - 428
  • [50] A new enantioselective route to bisabolane sesquiterpenes phenols: Synthesis of (S)-(+)-Curcuphenol and (S)-(+)-curcumene
    Fuganti, C
    Serra, S
    SYNLETT, 1998, (11) : 1252 - +