Total synthesis of (-)-periplanones C and D. Their pheromonal activities against three Periplaneta species

Tetrahedron

Volumn 53, Issue 21, 1997, Pages 7209-7218

  Nishii, Yoshinori ^a   Watanabe, Keisuke ^b   Yoshida, Taichi ^a   Okayama, Tatsutoshi ^a   Takahashi, Shozo ^c   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b SUMITOMO CHEMICAL CO LTD   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PERIPLANONE C; PERIPLANONE D; PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; COCKROACH; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; GAS CHROMATOGRAPHY; IN VITRO STUDY; INSECT; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SPECIES DIFFERENCE; STEREOCHEMISTRY;

EID: 0030915732     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00424-9     Document Type: Article

References (29)

1. a) Persoons, C. J.; Ritter, F. J.; Verwiel, P. E. J.; Hauptmann, H.; Mori, K. Tetrahedron Lett., 1990, 31, 1747-1750.
2. References are cited therein. Another recent studies: b) Takahashi, T.; Kanda, Y.; Nemoto, H.; Kitamura, K.; Tsuji, J.; Fukuzawa, Y. J. Org. Chem., 1986, 51, 3393-3394.
3. c) Cauwberghs, S. G.; De Clercq, P. J. Tetrahedron Lett., 1988, 29, 6501-6504.
4. d) Harada, T.; Takahashi, T.; Takahashi, S.; Tetrahedron Lett., 1992, 33, 369-372.
5. e) Shimazaki, K.; Mori, M.; Okada, K.; Chuman, T.; Goto, H.; Osawa, E.; Sakakibara, K.; Hirota, M. J. Chem. Soc. Perkin Trans. 2, 1992, 811-818.
6. f) Shimazaki, K.; Mori, M.; Okada, K.; Chuman, T.; Kuwahara, S.; Kitahara, T.; Mori, K.; Goto, H.; Osawa, E.; Sakakibara, K.; Hirota, M. J. Chem. Soc. Perkin Trans. 2, 1993, 1167-1173.
7. g) McMurry, J. E.; Siemers, N. O. Tetrahedron Lett., 1994, 35, 4505-4508.
8. h) Sakakibara, K.; Kawamura, H.; Nagata, T.; Ren, J.; Hirota, M.; Shimazaki, K.; Chuman, T. Bull. Chem. Soc. Jpn., 1994, 67, 2768-2778.
9. i) De Geyter, T.; Cauwberghs, S. G.; De Clercq, P. J. Bull. Soc. Chim. Belg., 1994, 103, 433-442.
10. j) Jonas, D.; Oezlue, Y.; Parsons, P. J. Synlett, 1995, 255-256.
11. k) Hashimoto, S.; Miyazaki, Y.; Shiro, M.; Ikegami, S. Chem. Lett., 1995, 1091-1902.
12. Takahashi, S.; Watanabe, K.; Saito, S.; Nomura, Y. Appl. Entomol. Zool., 1995, 30, 357-360.
13. Biendl, M.; Hauptmann, H.; Sass, H. Tetrahedron Lett., 1989, 30, 2367-2368.
14. a) Tanabe, Y.; Suzukamo, G.; Komuro, Y.; Imanishi, N.; Morooka, S.; Enomoto, M.; Kojima, A.; Sanemitsu, Y.; Mizutani, M. Tetrahedron Lett., 1991, 32, 379-382.
15. b) Tanabe, Y.; Kubota, Y.; Sanemitsu, Y.; Itaya, N.; Suzukamo, G. Tetrahedron Lett., 1991, 32, 383-386.
16. c) Tanabe, Y.; Yamamoto, H.; Murakami, M.; Yanagi, K.; Kubota, Y.; Okumura, H.; Suzukamo, G. J. Chem. Soc., Perkin Trans. 1, 1995, 935-947.
17. d) Nishii, Y.; Matsumura, H.; Muroya, Y.; Tsuchiya, T.; Tanabe, Y. Biosci. Biotech. Biochem., 1995, 59, 1355-1357.
18. e) Tanabe, Y.; Okumura, H.; Nagaosa, M.; Murakami, M. Bull. Chem. Soc. Jpn., 1995, 68, 1467-1472.
19. f) Nishii, Y.; Wakimura, K.; Tsuchiya, T.; Nakamura, S.; Tanabe, Y. J. Chem. Soc., Perkin Trans. 1, 1996, 1243-1249.
20. g) Tanabe, Y.; Seko, S.; Nishii, Y.; Yoshida, T.; Utsumi, N.; Sanemitsu, Y.; Suzukamo, G. J. Chem. Soc., Perkin Trans.1, 1996, 2157-2166.
21. h) Nishii, Y.; Tanabe, Y. J. Chem. Soc., Perkin Trans.1, 1997, 477-486.
22. a) Shizuri, Y.; Yamagichi, S.; Yamamura, S.; Ishihara, M.; Ohba, S.; Saito, Y.; Niwa, M.; Terada, Y.; Miyazaki, M. Tetrahedron Lett., 1987, 28, 3831-3834.
23. b) Shizuri, Y.; Matsunaga, K.; Tamaki, K.; Yamaguchi, S.; Yamamura, S. Tetrahedron Lett., 1988, 29, 1971-1974.
24. Purchased from Ogawa Perfume Co. Ltd.
25. Nishii, Y.; Yoshida, T.; Tanabe, Y. Biosci. Biotech. Biochem., 1997, 61, 547-548.
26. a) Fattorusso, E.; Magno, S.; Mayol, L.; Amico, V.; Oriente, G.; Piattelli, M.; Tringali, C. Tetrahedron Lett., 1978, 4149-4152.
27. b) Nagashima, F.; Toyota, M.; Asakawa, Y. Phytochemistry, 1990, 29, 2169-2174.
28. Still, W. C. J. Am. Chem. Soc., 1979, 101, 2493-2495.
29. 2·HCl (1.8 molar amounts) was found to give good result after the optimization in our hands.