A Short Synthesis of Bisabolane Sesquiterpenes

被引:12
|
作者
Du, Zhen-Ting [1 ,2 ]
Zheng, Shuai [1 ]
Chen, Gang [1 ]
Lv, Dong [1 ]
机构
[1] NW A&F Univ, Coll Sci, Yangling 712100, Shaanxi, Peoples R China
[2] Talimu Univ, Key Lab Protect & Utilizat Biol Resources Tarim B, Alaer 843300, Xinjiang, Peoples R China
基金
中国国家自然科学基金;
关键词
curcumene; xanthorrhizol; curcuhydroquinone; synthesis; MEDIATED ENANTIOSELECTIVE SYNTHESIS; CLAISEN REARRANGEMENT APPROACH; CURCUMA-XANTHORRHIZA; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; (+/-)-CURCUPHENOL; ACID; (+/-)-CURCUHYDROQUINONE; (+)-ALPHA-CURCUMENE; (-)-XANTHORRHIZOL;
D O I
10.3390/molecules16098053
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (+/-)-curcumene, (+/-)-xanthorrhizol and (+/-)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials. The halogen-lithium exchange followed by addition of isoprenylacetone and reduction of the obtained carbinols are the key steps of the synthetic pathway. This synthetic approach provides a new route to the bisabolane sesquiterpenes.
引用
收藏
页码:8053 / 8061
页数:9
相关论文
共 50 条
  • [1] A NOVEL METHOD FOR SYNTHESIS OF BISABOLANE SESQUITERPENES - ORGN
    CRAWFORD, RJ
    ERMAN, WF
    BROADDUS, CD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1970, : 30 - &
  • [2] METALATION OF LINONENE - NOVEL METHOD FOR SYNTHESIS OF BISABOLANE SESQUITERPENES
    CRAWFORD, RJ
    BROADDUS, CD
    FERMAN, WF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) : 4298 - &
  • [3] Synthesis of bisabolane sesquiterpenes:A Johnson-Claisen rearrangement approach
    Zhen Ting Du~(a
    ChineseChemicalLetters, 2010, 21 (07) : 813 - 815
  • [4] Synthesis of bisabolane sesquiterpenes: A Johnson-Claisen rearrangement approach
    Du, Zhen Ting
    Yu, Hong Rui
    Xu, Yan
    Li, Yong
    Li, An Pai
    CHINESE CHEMICAL LETTERS, 2010, 21 (07) : 813 - 815
  • [5] Bisabolane sesquiterpenes from Ligularia dentata
    Gao, K
    Yang, L
    Jia, ZJ
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1997, 36 (08): : 715 - 718
  • [6] BISABOLANE HALOGENATED SESQUITERPENES FROM LAURENCIA
    NORTE, M
    FERNANDEZ, JJ
    PADILLA, A
    PHYTOCHEMISTRY, 1992, 31 (01) : 326 - 327
  • [7] Bisabolane sesquiterpenes:: Synthesis of (R)-(+)-sydowic acid and (R)-(+)curcumene ether
    Serra, S
    SYNLETT, 2000, (06) : 890 - 892
  • [8] Bisabolane sesquiterpenes from Ligularia thyrsoidea
    Liao, JC
    Zhu, QX
    Yang, H
    Jia, ZJ
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1999, 46 (02) : 185 - 190
  • [9] Bisabolane sesquiterpenes from the roots of Ligularia cymbulifera
    Liu, CM
    Fei, DQ
    Wu, QH
    Gao, K
    JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04): : 695 - 699
  • [10] New bisabolane sesquiterpenes from Ligularia songarica
    Fu, B
    Yang, L
    Yang, XP
    Li, XP
    Jia, ZJ
    PHARMAZIE, 2000, 55 (12): : 947 - 952