Synthesis and insect antifeedant activity of 2-substituted 2,3-dihydrofuran-3-ols and butenolides (part II).

被引:0
|
作者
Gebbinck, EAK [1 ]
Stork, GA [1 ]
Jansen, BJM [1 ]
de Groot, A [1 ]
机构
[1] Agr Univ Wageningen, Res Ctr, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands
关键词
alkylation; cyanohydrins; furanones; antifeedants;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The introduction of a hydroxy group at C-13 of the clerodane skeleton is proposed as a strategy to potentially increase the antifeedant activity of simple analogs. This idea is applied to clerodane analogs with furan or butenolide type sidechains and therefore syntheses were developed for several types of 3-alkyl-substituted butenolides, 3-alkyl-substituted-3-hydroxybutenolides and 3-hydroxytetrahydrofuran derivatives. The antifeedant activity was tested on 5th instar larvae of Pieris brassicae. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:11077 / 11094
页数:18
相关论文
共 50 条
  • [31] Synthesis, structure and chemical properties of N-substituted 2(3)-imino-2,3-dihydrofuran-3(2)-ones (Review)
    Zalesov, VV
    Rubtsov, AE
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (02): : 163 - 186
  • [32] Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library
    Song, Buer
    Nie, Lifei
    Bozorov, Khurshed
    Kuryazov, Rustamkhon
    Zhao, Jiangyu
    Aisa, Haji Akber
    MOLECULAR DIVERSITY, 2023, 27 (04) : 1767 - 1783
  • [33] A CONVENIENT SYNTHESIS OF 2-SUBSTITUTED AND 2,3-SUBSTITUTED 4H-CHROMEN-4-ONES
    HIRAO, I
    YAMAGUCHI, M
    HAMADA, M
    SYNTHESIS-STUTTGART, 1984, (12): : 1076 - 1078
  • [34] SYNTHESIS AND ANTICANCER ACTIVITY OF 2-SUBSTITUTED 2,3-DIHYDRO-1,3,2-BENZOXAZAPHOSPHORIN-4-ONE AND ITS 2-OXIDE DERIVATIVES
    KOSTKA, K
    PORADA, M
    GRACZYK, J
    ARCHIV DER PHARMAZIE, 1994, 327 (04) : 233 - 236
  • [35] A rapid synthesis of thieno[2,3-c]pyridine and 2-substituted thieno[2,3-c]pyridines
    Graulich, A
    Liégeois, JF
    SYNTHESIS-STUTTGART, 2004, (12): : 1935 - 1937
  • [36] A new series of 2-substituted 3-phosphonic derivatives of chromone.: Part II.: Synthesis, in vitro alkylating and in vivo antitumour activity
    Budzisz, E
    Graczyk-Wojciechowska, J
    Zieba, R
    Nawrot, B
    NEW JOURNAL OF CHEMISTRY, 2002, 26 (12) : 1799 - 1804
  • [37] Efficient synthesis of 2-substituted 2,3-dihydro-4-quinolones as potential intermediates for 2-substituted 1,2,3,4-tetrahydro-4-quinolone antitumor agents
    Sun Choi
    Keumnyeo Jung
    Jaesang Ryu
    Archives of Pharmacal Research, 2006, 29 : 369 - 374
  • [38] Efficient synthesis of 2-substituted 2,3-dihydro-4-quinolones as potential intermediates for 2-substituted 1,2,3,4-tetrahydro-4-quinolone antitumor agents
    Choi, Sun
    Jung, Keumnyeo
    Ryu, Jaesang
    ARCHIVES OF PHARMACAL RESEARCH, 2006, 29 (05) : 369 - 374
  • [39] Regioselective synthesis of 2-substituted 3-diarylmethylenylpiperidines
    Chang, Meng-Yang
    Lin, Chung-Han
    Lee, Tein-Wei
    TETRAHEDRON LETTERS, 2012, 53 (06) : 627 - 631
  • [40] SYNTHESIS OF 2-SUBSTITUTED ISOTHIAZOLOPYRIDIN-3-ONES
    BAGGALEY, KH
    JENNINGS, LJA
    TYRRELL, AWR
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (06) : 1393 - 1396