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

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 1, 2006, Pages 303-306

  Abe, Masaki ^a   Imai, Tetsuya ^a   Ishii, Naoki ^a   Usui, Makio ^a  

^a OTSUKA CHEMICAL CO LTD   (Japan)

Author keywords

Acyl migration reaction; Dehydrogenation; Insecticidal activity; Quinolactacide

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; DEHYDROGENATION; DERIVATIVES; ESTERS; MANGANESE COMPOUNDS;

ACYL MIGRATION REACTION; INSECTICIDAL ACTIVITY; MANGANESE OXIDE; QUINOLACTIDES;

SUGARS;

INSECTICIDE; MANGANESE DERIVATIVE; MANGANESE DIOXIDE; OXIDE; QUINOLACTACIDE; QUINOLONE DERIVATIVE;

ACYLATION; ANIMAL; APHID; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HYDROGENATION; MOTH; SYNTHESIS;

ACYLATION; ANIMALS; APHIDS; HYDROGENATION; INSECTICIDES; MANGANESE COMPOUNDS; MOLECULAR STRUCTURE; MOTHS; OXIDES; QUINOLONES;

APHIDIDAE; LEPIDOPTERA; MYZUS PERSICAE; PENICILLIUM CITRINUM; PLUTELLA XYLOSTELLA; PRUNUS PERSICA;

EID: 31444456019     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.70.303     Document Type: Article

References (10)

1. Abe, M., Imai, T., Ishii, N., Usui, M., Okuda, T., and Oki, T., Quinolactacide, a new quinolone insecticide from Penicillium citrinum Thom F 1539. Biosci. Biotechnol. Biochem., 69, 1202-1205 (2005).
2. Kakinuma, N., Iwai, H., Takahashi, S., Hamano, K., Yanagisawa, T., Nagai, K., Tanaka, K., Suzuki, K., Kirikae, F., Kirikae, T., and Nakagawa, A., Quinolactacins A, B and C: novel quinolone compounds from Penicillium sp. EPF-6 I. Taxonomy, production, isolation and biological properties. J. Antibiotics, 53, 1247-1251 (2000).
3. Takahashi, S., Kakinuma, N., Iwai, H., Yanagisawa, T., Nagai, K., Suzuki, K., and Tokunaga, T., Quinolactacins A, B and C: novel quinolone compounds from Penicillium sp. EPF-6 II. Physico-chemical properties and structure elucidation. J. Antibiotics, 53, 1252-1256 (2000).
4. Nakagawa, A., Japan Kokai Tokkyo Koho, 2001-247571 (Sept. 11, 2001).
5. Kim, W., Song, N., and Yoo, I., Quinolactacins A1 and A2, new acetylcholinesterase inhibitors from Penicillium citrinum. J. Antibiotics, 54, 831-835 (2001).
6. Tatsuta, K., Misawa, H., and Chikauchi, K., Biomimetic total synthesis of quinolactacin B, TNF production inhibitor, and its analogs. J. Antibiotics, 54, 109-112 (2001).
7. Zhang, X., Jiang, W., and Sui, Z., Concise enantioselective syntheses of quinolactacins A and B through alternative Winterfeldt oxidation. J. Org. Chem., 68, 4523-4526 (2003).
8. Fischer, R., Bretschneider, T., Krüger, W. B., Ruther, M., Erdelen, C., Wachendorff-Neumann, U., Santel, J. H., and Dollinger, M., European Patent 0668267 (Aug. 23, 1995).
9. Nakamura, U., Permer, J. C., Kikukawa, H., Sano, M., and Ohno, K., Japan Kokai Tokkyo Koho, 2001-335573 (Dec. 4, 2001).
10. Kashdan, S. D., Schwartz, A. J., and Rapoport, H., Synthesis of 1,2,3,4-tetrahydroisoquinolines. J. Org. Chem., 47, 2638-2643 (1982).