Synthesis and absolute stereochemistry of marine nor-sesquiterpene austrodoric acid

被引:19
|
作者
Kulcitki, V [1 ]
Ungur, N [1 ]
Gavagnin, M [1 ]
Carbone, M [1 ]
Cimino, G [1 ]
机构
[1] CNR, Ist Chim Biomol, I-80078 Pozzuoli, NA, Italy
关键词
D O I
10.1016/j.tetasy.2003.10.024
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An enantiospecific synthesis of the nor-sesquiterpene austrodoric acid 1, recently isolated from an Antarctic marine mollusk, has been achieved. The synthetic strategy was based on the ring contraction of a suitable homo-drimanic epoxide,3, easily obtained from commercial (+)-sclareolide 4. The absolute configuration of natural austrodoric acid, not determined previously, has been now established by analyzing the CD profile of synthetic 1, which was the same as the natural compound. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:423 / 428
页数:6
相关论文
共 50 条
  • [1] First enantiospecific synthesis of marine nor-sesquiterpene (+)-austrodoral from (-)-sclareol
    Alvarez-Manzaneda, EJ
    Chahboun, R
    Barranco, I
    Torres, EC
    Alvarez, E
    Alvarez-Manzaneda, R
    TETRAHEDRON LETTERS, 2005, 46 (32) : 5321 - 5324
  • [2] Studies on the synthesis of (±)-pathylactone A, a nor-sesquiterpene lactone isolated from marine sources
    Coelho, F
    Diaz, G
    TETRAHEDRON, 2002, 58 (09) : 1647 - 1656
  • [3] Jasonone, a Nor-sesquiterpene from Jasonia montana
    Mohamed, Abou El-Hamd H.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2007, 62 (01): : 125 - 128
  • [4] Absolute configuration of birkenal, a nor-sesquiterpene aldehyde from essential oil of Betula pubescens buds
    Domrachev, D. V.
    Tkachev, A. V.
    CHEMISTRY OF NATURAL COMPOUNDS, 2006, 42 (03) : 304 - 306
  • [5] Absolute configuration of birkenal, A nor-sesquiterpene aldehyde from essential oil of Betula pubescens buds
    D. V. Domrachev
    A. V. Tkachev
    Chemistry of Natural Compounds, 2006, 42 : 304 - 306
  • [6] A new nor-sesquiterpene lactone from Ainsliaea fulvioides
    Yan Wang~a
    Chinese Chemical Letters, 2009, 20 (05) : 586 - 588
  • [7] A new nor-sesquiterpene lactone from Ainsliaea fulvioides
    Wang, Yan
    Xu, Ming Lu
    Jin, Hui Zi
    Fu, Jian Jun
    Hu, Xiao Jia
    Qin, Jiang Jiang
    Yan, Shi Kai
    Shen, Yun Heng
    Zhang, Wei Dong
    CHINESE CHEMICAL LETTERS, 2009, 20 (05) : 586 - 588
  • [8] STRUCTURE AND STEREOCHEMISTRY OF MEXICANIN-F, A NOVEL DIMERIC NOR-SESQUITERPENE LACTONE FROM HELENIUM-MEXICANUM
    DEVIVAR, AR
    DELGADO, G
    TETRAHEDRON LETTERS, 1985, 26 (05) : 579 - 582
  • [9] Unusual nor-sesquiterpene lactone from the fruits of Illicium henryi
    Liu, Ji-Feng
    Wang, Ya-Feng
    Bi, Ya-Ping
    Li, Hui-Juan
    Jia, Lu
    Bi, Yue-Feng
    Zhang, Yan-Bing
    TETRAHEDRON LETTERS, 2013, 54 (36) : 4834 - 4836
  • [10] SECO-SESQUITERPENE AND NOR-SESQUITERPENE LACTONES WITH A NEW CARBON SKELETON FROM ARTEMISIA-SANTOLINIFOLIA
    JAKUPOVIC, J
    TAN, RX
    BOHLMANN, F
    JIA, ZJ
    HUNECK, S
    PHYTOCHEMISTRY, 1991, 30 (06) : 1941 - 1946