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

被引:22
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
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 [J].
Abe, M ;
Imai, T ;
Ishii, N ;
Usui, M ;
Okuda, T ;
Oki, T .
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 [J].
Kakinuma, N ;
Iwai, H ;
Takahashi, S ;
Hamano, K ;
Yanagisawa, T ;
Nagai, K ;
Tanaka, K ;
Suzuki, K ;
Kirikae, F ;
Kirikae, T ;
Nakagawa, A .
JOURNAL OF ANTIBIOTICS, 2000, 53 (11) :1247-1251
[4]   SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES [J].
KASHDAN, DS ;
SCHWARTZ, JA ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2638-2643
[5]   Quinolactacins A1 and A2, new acetylcholinesterase inhibitors from Penicillium citrinum [J].
Kim, WG ;
Song, NK ;
Yoo, ID .
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 [J].
Takahashi, S ;
Kakinuma, N ;
Iwai, H ;
Yanagisawa, T ;
Nagai, K ;
Suzuki, K ;
Tokunaga, T ;
Nakagawa, A .
JOURNAL OF ANTIBIOTICS, 2000, 53 (11) :1252-1256
[9]   Biomimetic total synthesis of quinolactacin B, TNF production inhibitor, and its analogs [J].
Tatsuta, K ;
Misawa, H ;
Chikauchi, K .
JOURNAL OF ANTIBIOTICS, 2001, 54 (01) :109-112
[10]   Concise enantioselective syntheses of quinolactacins A and B through alternative Winterfeldt oxidation [J].
Zhang, XQ ;
Jiang, WQ ;
Sui, ZH .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4523-4526