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
  • [1] Highly efficient synthesis of the optically active sesquiterpene hydroquinone (+)-zonarol and the sesquiterpene quinone (+)-zonarone
    Villamizar, J
    Orcajo, AL
    Fuentes, J
    Tropper, E
    Alonso, R
    JOURNAL OF CHEMICAL RESEARCH-S, 2002, (08): : 395 - 397
  • [2] STEREOSELECTIVE TOTAL SYNTHESES OF FUNGITOXIC HYDROQUINONES (+/-)-ZONAROL AND (+/-)-ISOZONAROL
    WELCH, SC
    RAO, ASCP
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10): : 1957 - 1961
  • [3] Total synthesis of the marine sesquiterpene quinones hyatellaquinone and spongiaquinone
    Bernet, A
    Schröder, J
    Seifert, K
    HELVETICA CHIMICA ACTA, 2003, 86 (06) : 2009 - 2020
  • [4] Synthesis and pharmacological activities of some sesquiterpene quinones and hydroquinones
    Laube, Thorsten
    Bernet, Andreas
    Dahse, Hans-Martin
    Jacobsen, Ilse D.
    Seifert, Karlheinz
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (04) : 1422 - 1427
  • [5] Total synthesis of yahazunol, zonarone and isozonarone
    Laube, T
    Schröder, J
    Stehle, R
    Seifert, K
    TETRAHEDRON, 2002, 58 (21) : 4299 - 4309
  • [6] Sesquiterpene Quinones/Hydroquinones from the Marine Sponge Spongia pertusa Esper
    Li, Jing
    Gu, Bin-Bin
    Sun, Fan
    Xu, Jian-Rong
    Jiao, Wei-Hua
    Yu, Hao-Bing
    Han, Bing-Nan
    Yang, Fan
    Zhang, Xi-Chun
    Lin, Hou-Wen
    JOURNAL OF NATURAL PRODUCTS, 2017, 80 (05): : 1436 - 1445
  • [7] MARINE SESQUITERPENE QUINONES AND HYDROQUINONES - ACID-CATALYZED REARRANGEMENTS AND STEREOCHEMICAL INVESTIGATIONS
    URBAN, S
    CAPON, RJ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) : 1023 - 1029
  • [8] Deoxyspongiaquinones: New sesquiterpene quinones and hydroquinones from a southern Australian marine sponge Euryspongia sp
    Urban, S
    Capon, RJ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1996, 49 (05) : 611 - 615
  • [9] Sesquiterpene Benzoxazoles and Sesquiterpene Quinones from the Marine Sponge Dactylospongia elegans
    Ovenden, Simon P. B.
    Nielson, Jonathan L.
    Liptrot, Catherine H.
    Willis, Richard H.
    Tapiolas, Dianne M.
    Wright, Anthony D.
    Motti, Cherie A.
    JOURNAL OF NATURAL PRODUCTS, 2011, 74 (01): : 65 - 68
  • [10] Total synthesis of the marine sesquiterpene quinone (-)-cyclozonarone
    Schröder, J
    Matthes, B
    Seifert, K
    TETRAHEDRON LETTERS, 2001, 42 (46) : 8151 - 8152