Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide

被引：58
|
作者：
Adlington, RM
Baldwin, JE
Mayweg, AVW
Pritchard, GJ
机构：
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 17期
关键词：
D O I：
10.1021/ol026467r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A study toward a possible biomimetic hetero Diels-Alder reaction is reported between humulene and a novel tropolone ortho-quinone methide. A suitable tropolone ortho-quinone methide precursor has been prepared from 3-methyl-2-furoate. Heating the ortho-quinone methide precursor gave a tropolone ortho-quinone methide, which in the presence of humulene underwent a hetero Diels-Alder reaction to give a deoxy analogue of epolone B.
引用
收藏
页码：3009 / 3011
页数：3
相关论文
共 50 条
  • [21] An Isolable Vinylidene ortho-Quinone Methide: Synthesis, Structure and Reactivity
    Liu, Hong
    Li, Kai
    Huang, Shengli
    Yan, Hailong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (20)
  • [22] An ortho-Quinone Methide Mediates Disulfide Migration in the Biosynthesis of Epidithiodiketopiperazines
    Fan, Jie
    Ran, Huomiao
    Wei, Peng-Lin
    Li, Yuanyuan
    Liu, Huan
    Li, Shu-Ming
    Yin, Wen-Bing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)
  • [23] Biocatalyst-initiated ortho-quinone methide generation and diversification
    Perkins, Jonathan
    Doyon, Tyler
    Romero, Evan
    Dockrey, Summer Baker
    Skinner, Kevin
    Zimmerman, Paul
    Narayan, Alison
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [24] Ortho-quinone methide driven synthesis of kynurenic acid lactams
    Sarik, Julian Robin
    Hetenyi, Anasztazia
    Berkecz, Robert
    Szatmari, Istvan
    Lorinczi, Balint
    RSC ADVANCES, 2024, 14 (31) : 22123 - 22131
  • [25] Synthesis of fused-ring systems and diarylmethane flavonoids via ortho-quinone methide intermediates
    Nuraini, Vidia A.
    Falasca, Valerio
    Wenholz, Daniel S.
    Black, David StC.
    Kumar, Naresh
    RSC ADVANCES, 2025, 15 (04) : 2912 - 2929
  • [26] STEREOSPECIFIC INTRAMOLECULAR DIELS-ALDER REACTION OF AN ORTHO-QUINONE METHIDE
    TALLEY, JJ
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) : 1695 - 1699
  • [27] An ortho-quinone methide based strategy towards the rubromycin spiroketal family
    Willis, N. J.
    Bray, C. D.
    RSC ADVANCES, 2015, 5 (98): : 80212 - 80215
  • [28] Nonenzymatic Self-Assembly Access to Diverse ortho-Quinone Methide-Based Pseudonatural Products
    Wu, Guangwei
    Qian, Xuan
    Huang, Yeqiang
    Liu, Yujia
    Zhou, Luning
    Wang, Wei
    Li, Jing
    Zhu, Tianjiao
    Gu, Qianqun
    Li, Dehai
    ORGANIC LETTERS, 2022, 24 (28) : 5235 - 5239
  • [29] ortho-Quinone Methides in Natural Product Synthesis
    Willis, Nicky J.
    Bray, Christopher D.
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) : 9160 - 9173
  • [30] Mechanistic Features of Asymmetric Vinylidene ortho-Quinone Methide Construction and Subsequent Transformations
    Xu, Da
    Chang, Yu
    Liu, Yidong
    Qin, Wenling
    Yan, Hailong
    ACS CATALYSIS, 2023, 13 (05) : 2957 - 2967
12345