Biogenetically Inspired Synthesis of Lingzhiol

被引:35
作者
Gautam, Krishna Sharmah [1 ]
Birman, Vladimir B. [1 ]
机构
[1] Washington Univ, Dept Chem, Campus Box 1134,One Brookings Dr, St Louis, MO 63130 USA
基金
美国国家科学基金会;
关键词
D O I
10.1021/acs.orglett.5b03212
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise stereo- and enantioselective synthesis of lingzhiol has been achieved featuring a biogenetically inspired Bronsted acid catalyzed semipinacol rearrangement of a glycidyl alcohol intermediate.
引用
收藏
页码:1499 / 1501
页数:3
相关论文
共 17 条
  • [1] ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES
    BOLM, C
    EWALD, M
    FELDER, M
    SCHLINGLOFF, G
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1169 - 1190
  • [2] Concise synthesis of (±)-Lingzhiol via epoxy-arene cyclization
    Chen, Dong
    Liu, Hao-Miao
    Li, Ming-Ming
    Yan, Yong-Min
    Xu, Wen-Dan
    Li, Xiao-Nian
    Cheng, Yong-Xian
    Qin, Hong-Bo
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (78) : 14594 - 14596
  • [3] Cheng Y., 2013, [No title captured], Patent No. [CN103435580A, 103435580]
  • [4] Fukuda O, 2001, ADV SYNTH CATAL, V343, P809, DOI 10.1002/1615-4169(20011231)343:8<809::AID-ADSC809>3.0.CO
  • [5] 2-1
  • [6] GAWLEY RE, 1976, SYNTHESIS-STUTTGART, P777
  • [7] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS
    GEMAL, AL
    LUCHE, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) : 5454 - 5459
  • [8] STUDIES ON INTRA-MOLECULAR ALKYLATION .10. ACID-CATALYZED REACTIONS OF 5,8-DIALKOXY-1,2,3,4-TETRAHYDRONAPHTHYL DIAZOMETHYL KETONES
    JOHNSON, DW
    MANDER, LN
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (07) : 1561 - 1568
  • [9] Li X, 2003, SYNLETT, P623
  • [10] Asymmetric total synthesis of (-)-lingzhiol via a Rh-catalysed [3+2] cycloaddition
    Long, Rong
    Huang, Jun
    Shao, Wenbin
    Liu, Song
    Lan, Yu
    Gong, Jianxian
    Yang, Zhen
    [J]. NATURE COMMUNICATIONS, 2014, 5