Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone

被引:21
|
作者
Schröder, J [1 ]
Magg, C [1 ]
Seifert, K [1 ]
机构
[1] Univ Bayreuth, Lehrstuhl Organ Chem 12, D-95440 Bayreuth, Germany
关键词
terpenes; phenols; quinones;
D O I
10.1016/S0040-4039(00)00891-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the naturally occurring sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone was achieved starting from beta-ionone, which was transformed via (+)-albicanic acid to (+)-albicanal and (-)-drim-7-en-11-al. Coupling of the aldehydes with lithiated hydroquinone ethers and further modification of the coupling products led to the target molecules. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5469 / 5473
页数:5
相关论文
共 50 条
  • [21] Total Synthesis of Marine Sesquiterpene Quinones (+)-Cyclospongiaquinone-1 and (-)- Dehydrocyclospongiaquinone-1 with a Tetracyclic Benzo[a] xanthene Skeleton
    Takeda, Yuki
    Narita, Koichi
    Katoh, Tadashi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (04) : 901 - 907
  • [22] New access to sesquiterpene hydroquinones:: Synthesis of (+)-ent-chromazonarol
    Villamizar, J
    Plata, F
    Canudas, N
    Tropper, E
    Fuentes, J
    Orcajo, A
    SYNTHETIC COMMUNICATIONS, 2006, 36 (03) : 311 - 320
  • [23] SESQUITERPENE LACTONES - A TOTAL SYNTHESIS OF (+/-)QUADRONE
    DEWANCKELE, JM
    ZUTTERMAN, F
    VANDEWALLE, M
    TETRAHEDRON, 1983, 39 (20) : 3235 - 3244
  • [24] Bioactive sesquiterpene quinols and quinones from the marine sponge Dysidea avara
    Jiao, Wei-Hua
    Xu, Ting-Ting
    Gu, Bin-Bin
    Shi, Guo-Hua
    Zhu, Yan
    Yang, Fan
    Han, Bing-Nan
    Wang, Shu-Ping
    Li, Yu-Shan
    Zhang, Wei
    Li, Jia
    Lin, Hou-Wen
    RSC ADVANCES, 2015, 5 (106) : 87730 - 87738
  • [25] SESQUITERPENE LACTONES - TOTAL SYNTHESIS OF (+/-)-VERNOLEPIN AND (+
    GRIECO, PA
    NISHIZAWA, M
    OGURI, T
    BURKE, SD
    MARINOVIC, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (17) : 5773 - 5780
  • [26] SESQUITERPENE LACTONES - TOTAL SYNTHESIS OF (+/-)-VERNOLEPIN
    ZUTTERMAN, F
    DEWILDE, H
    MIJNGHEER, R
    DECLERCQ, P
    VANDEWALLE, M
    TETRAHEDRON, 1979, 35 (20) : 2389 - 2396
  • [27] A diastereoselective total synthesis of the sesquiterpene (±)-mutisianthol
    Ferraz, HMC
    Aguilar, AM
    Silva, LF
    TETRAHEDRON, 2003, 59 (31) : 5817 - 5821
  • [28] Stereoselective total synthesis of the sesquiterpene (±)-β-isocomene
    Schmidt, Arndt W.
    Olpp, Thomas
    Baum, Elke
    Stiffel, Tina
    Knoelker, Hans-Joachim
    SYNLETT, 2007, (15) : 2371 - 2374
  • [29] Chemoenzymatic total synthesis of the sesquiterpene (-)-patchoulenone
    Banwell, M
    McLeod, M
    CHEMICAL COMMUNICATIONS, 1998, (17) : 1851 - 1852
  • [30] TOTAL SYNTHESIS OF ACETYLENIC SESQUITERPENE FREELINGYNE
    KNIGHT, DW
    PATTENDEN, G
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (05) : 188 - 188