A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement

Tetrahedron

Volumn 52, Issue 25, 1996, Pages 8451-8470

  Kaga, Harumi ^a   Goto, Kouhei ^a   Takahashi, Tomiki ^a   Hino, Masao ^a   Tokuhashi, Takashi ^b   Orito, Kazuhiko ^b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CAPSAICIN DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENERGY METABOLISM; GENE REARRANGEMENT; NERVE CONDUCTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029951041     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00414-0     Document Type: Article

References (43)

1. For a review, see: (a) Suzuki, T.; Iwai, K. In The Alkaloids, Brossi, A., Ed.; Academic Press: Orlando, 1984; Vol. 27; pp. 227-299.
2. (b)Buck, S. H.; Burks, T. F. Pharmacol. Rev. 1986, 38, 179-226.
3. Jhamandas, K.; Yaksh, T. L.; Harty, G.; Szolcsanyi, J.; Go, V. L. W. Brain Res. 1984, 306, 215-225.
4. Gannett, P. M.; Nagel, D. L.; Reilly, P. J.; Lawson, T.; Sharpe, J.; Toth, B. J. Org. Chem. 1988, 53, 1064-1071.
5. Nagabhushan, M.; Bhide, S. V. Natr. Cancer 1986, 8, 201-210.
6. Toth, B.; Rogan, E.; Walker, B. Anticancer Res. 1984, 4, 117-120.
7. Kawada, T.; Watanabe, T.; Takaishi, T; Tanaka, T; Iwai, K. Proc. Soc. Exp. Biol. Med. 1986, 183, 250-251.
8. Watanabe, T.; Kawada, T.; Kurosawa, M.; Sato, A.; Iwai, K. Am. J. Physiol. 1988, 255, E23-E27.
9. Some of capsaicinoids remain as they were tentatively identified, as documented well in ref 1a.
10. Heresch, F.; Jurenittsch, J.; Chromatographica 1979, 12, 647-650.
11. Kopp, B.; Jurenitsch, J. R. Planta Medica 1981, 43, 272-279.
12. Sticher, O.; Soldati, F.; Joshi, R. K. J. Chromatogr. 1987, 166, 221-231.
13. Jurenitsch, J.; Wginger, R. Sci. Pharm. 1982, 50, 111-114.
14. Jurenitsch, J.; David, M.; Heresch, F.; Kubelka, W. Planta Medica 1979, 36, 61-67.
15. Bennett, D. J.; Kirby, G. W. J. Chem. Soc., (C) 1968, 442-447.
16. Kaga, H.; Miura, M.; Orito, K. J. Org. Chem. 1989, 54, 3477-3478.
17. Rangoonwala, R.; Seitz, G. Dtsch. Apoth. Ztg. 1970, 110, 1946-1949.
18. Späth, E.; Darings, S. F. Ber. Dtsch. Chem. Ges. 1930, 63, 737-743.
19. Takahashi, M.; Osawa, K.; Ueda, J.; Okada, K. Yakugaku Zasshi 1976, 96, 137-139.
20. Crombie, L.; Dandegaonker, S. H.; Simpson, K. B. J. Chem. Soc. 1955, 1025-1027.
21. Jezo, I. Chem. Zvesti 1975, 29, 714-718.
22. Synthesis of acids 8 via nitriles 5 or malonates 6 from alcohols 4 was attempted initially via the preparation of the corresponding bromides using phosphorus tribromide. However, we could not always obtain such good yields for the brominations as the 82% yield reported for that of 4Aa.: Vig, O. P.; Aggarwal, R. C.; Sharma, M. L.; Sharma, S. D. Indian J. Chem., Sect. B. 1979, 17B, 558-559.
23. Kocienski, P. J.; Lythgoe, B.; Waterhouse, I. J. Chem. Soc. 1980, 1045-1050.
24. Sonnet, P. E. J. Org. Chem. 1974, 39, 3793-3794 and references cited therein.
25. Kaga, H.; Goto, K.; Fukuda, T.; Orito, K. Biosci. Biotech. Biochem. 1992, 56, 946-948.
26. Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brockson, T. J.; Li, T.-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741-743.
27. Cyanation via tosylation was known. See: Cope, A. C.; Mehta, A. S. J. Am. Chem Soc. 1964, 86, 5626-5630.
28. Dihydrocapsaicinoids HC-9, HC-10, HC-11 has been prepared by us. Kaga, H.; Miura, M.; Orito, K. Synthesis 1989, 864-866.
29. Mutagenicity of synthetic capsaicinoids, C-9, C-10, C-11, HC-10, HC-11, and cis-C-10 was also tested, using S. typhimurium strains TA 98 and TA 100 with and without S9, but no significant activity was observed. Ohyama, T.; Jinn, K.; Kato, Y.; Chiba, Y.; Tsuzuki, T., Kaga, H.; Orito, K., unpublished results. For the reported data of mutagenicity of capsaicinoids see: ref. 3, 4 and 5.
30. (a) Rangoonwala, R. J. Chromatogr. 1969, 41, 265-266.
31. (b) Rangoonwala, R; Seitz, G. Deut. Apoth.-Ztg. 1969, 109, 273-275.
32. Panker, P. S.; Magar, N. G. J. Chromatogr. 1977, 144, 149-152.
33. Suzuki, T; Kawada, T.; Iwai, K. J. Chromatogr. 1980, 198, 217-223.
34. Jurenitsch, J. Sci. Pharm. 1982, 50, 64-70.
35. Masada, Y.; Hashimoto, K.; Inoue, T., Suzuki, M. J. Food Sci. 1971, 36, 858-860.
36. Jurenitsch, J.; Kubelka, W.; Jentzech, K. Sci. Pharm. 1978, 46, 307-318.
37. Jurenitsch, J. Sci. Pharm. 1979, 47, 31-36.
38. Jurenitsch, J. J. Chromatogr. 1980, 189, 398-397.
39. Jurenitsch, J. Sci. Pharm. 1981, 49, 321-328.
40. Jurenitsch, J.; Bingler, E.; Becker, H; Kubelka, W. Planta Med. 1979, 36, 54-60.
41. Jurenitsch, J.; Kampelmüler, I. J. Chromatogr. 1980, 193, 101-110.
42. 1H NMR and EI MS spectral data were essentially the same as that previously reported for samples contaminated with a small amount of the cis-isomer. See ref. 24.
43. 1H NMR (300 MHz) and EI MS spectral data have been reported. See ref. 3.