Towards the total synthesis of colletofragarones: constructing the macrocyclic lactone by high pressure-mediated intramolecular Diels-Alder reaction

被引:15
|
作者
Marrero, Joaquin G. [1 ]
Harwood, Laurence M. [1 ]
机构
[1] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
关键词
COLLETOTRICHUM-FRAGARIAE; ACID; INHIBITORS;
D O I
10.1016/j.tetlet.2009.03.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein an intramolecular Diels-Alder approach towards the construction of the macrocyclic lactone ring and the perhydrobenzofuran system of the colletofragarones, novel metabolites produced by fungi of the genus Colletotrichum that are responsible for inhibition of germination of the conidia in these species. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:3574 / 3576
页数:3
相关论文
共 50 条
  • [1] Towards the total synthesis of tangutorine by intramolecular Diels-Alder reaction
    Wilkinson, JA
    Ardes-Guisot, N
    Ducki, S
    Leonard, J
    TETRAHEDRON LETTERS, 2005, 46 (46) : 8053 - 8056
  • [2] Intramolecular Diels-Alder reaction with an α-methylene lactone as dienophile
    Maier, ME
    Perez, C
    SYNLETT, 1998, (02) : 159 - +
  • [3] Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diels-Alder Reaction
    Kamo, Shogo
    Kurosawa, Hitomi
    Matsuzawa, Akinobu
    Sugita, Kazuyuki
    ORGANIC LETTERS, 2022, 24 (03) : 921 - 923
  • [4] Microwave-Assisted Intramolecular Diels-Alder Reaction towards the Total Synthesis of Symbioimine
    Born, Stephen
    Bacani, Genesis
    Olson, Erin E.
    Kobayashi, Yoshihisa
    SYNLETT, 2008, (18) : 2877 - 2881
  • [5] Concise enantioselective synthesis of wine lactone via intramolecular Diels-Alder reaction
    Ohkubo, Yasutaka
    Masuda, Yui
    Ogura, Yusuke
    Takikawa, Hirosato
    Watanabe, Hidenori
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2021, 85 (06) : 1390 - 1394
  • [6] Concise enantioselective synthesis of wine lactone via intramolecular Diels-Alder reaction
    Ohkubo, Yasutaka
    Masuda, Yui
    Ogura, Yusuke
    Takikawa, Hirosato
    Watanabe, Hidenori
    Bioscience, Biotechnology and Biochemistry, 2021, 85 (06): : 1390 - 1394
  • [7] Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides
    Rogachev, Victor O.
    Metz, Peter
    NATURE PROTOCOLS, 2006, 1 (06) : 3076 - 3087
  • [8] THE HIGH-PRESSURE MEDIATED INTRAMOLECULAR DIELS-ALDER REACTION OF FURAN DIENES - A SYNTHETIC APPROACH TOWARDS DAPHNANES
    HARWOOD, LM
    LEEMING, SA
    ISAACS, NS
    TETRAHEDRON LETTERS, 1985, 26 (18) : 2229 - 2232
  • [9] Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels-Alder Reaction
    Han, Jing-Chun
    Liu, Lian-Zhu
    Chang, Yuan-Yuan
    Yue, Guo-Zong
    Guo, Jie
    Zhou, Li-Yan
    Li, Chuang-Chuang
    Yang, Zhen
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5492 - 5504
  • [10] A concise total synthesis of (±)-bakkenolide A by means of an intramolecular Diels-Alder reaction
    Back, TG
    Payne, JE
    ORGANIC LETTERS, 1999, 1 (04) : 663 - 665