Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities

被引：21
作者：
Abe, M [1 ]
Imai, T [1 ]
Ishii, N [1 ]
Usui, M [1 ]
机构：
[1] Otsuka Chem Co Ltd, Naruto Res Ctr, Naruto, Tokushima 7728601, Japan
来源：
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2006年 / 70卷 / 01期
关键词：
quinolactacide; insecticidal activity; acyl migration reaction; dehydrogenation;
D O I：
10.1271/bbb.70.303
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Quinolactacide isolated from Penicillium citrinum F 1539 was synthesized and evaluated for its insecticidal activities. The key steps of the total synthesis were an acyl migration reaction of the enol ester intermediate and dehydrogenation of tetrahydroquinolactacide with manganese dioxide. The synthesized quinolactacide showed 100% and 42% mortality against the green peach aphid (Myzus persicae) and diamondback moth (Plutella xylostella) at 500 ppm, respectively.
引用
收藏
页码：303 / 306
页数：4
相关论文
共 10 条
  • [1] Quinolactacide, a new quinolone insecticide from Penicillium citrinum Thom F 1539
    Abe, M
    Imai, T
    Ishii, N
    Usui, M
    Okuda, T
    Oki, T
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2005, 69 (06) : 1202 - 1205
  • [2] FISCHER R, 1995, Patent No. 0668267
  • [3] Quinolactacins A, B and C:: Novel quinolone compounds from Penicillium sp EPF-6 I.: Taxonomy, production, isolation and biological properties
    Kakinuma, N
    Iwai, H
    Takahashi, S
    Hamano, K
    Yanagisawa, T
    Nagai, K
    Tanaka, K
    Suzuki, K
    Kirikae, F
    Kirikae, T
    Nakagawa, A
    [J]. JOURNAL OF ANTIBIOTICS, 2000, 53 (11) : 1247 - 1251
  • [4] SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES
    KASHDAN, DS
    SCHWARTZ, JA
    RAPOPORT, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) : 2638 - 2643
  • [5] Quinolactacins A1 and A2, new acetylcholinesterase inhibitors from Penicillium citrinum
    Kim, WG
    Song, NK
    Yoo, ID
    [J]. JOURNAL OF ANTIBIOTICS, 2001, 54 (10) : 831 - 835
  • [6] NAKAGAWA A, 2001, Patent No. 2001247571
  • [7] NAKAMURA U, 2001, Patent No. 2001335573
  • [8] Quinolactacins A, B and C:: Novel quinolone compounds from Penicillium sp EPF-6 II.: Physico-chemical properties and structure elucidation
    Takahashi, S
    Kakinuma, N
    Iwai, H
    Yanagisawa, T
    Nagai, K
    Suzuki, K
    Tokunaga, T
    Nakagawa, A
    [J]. JOURNAL OF ANTIBIOTICS, 2000, 53 (11) : 1252 - 1256
  • [9] Biomimetic total synthesis of quinolactacin B, TNF production inhibitor, and its analogs
    Tatsuta, K
    Misawa, H
    Chikauchi, K
    [J]. JOURNAL OF ANTIBIOTICS, 2001, 54 (01) : 109 - 112
  • [10] Concise enantioselective syntheses of quinolactacins A and B through alternative Winterfeldt oxidation
    Zhang, XQ
    Jiang, WQ
    Sui, ZH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4523 - 4526
1