Convenient methods for regio- and/or chemo-selective O-deacylation of taxinine, a naturally occurring taxane diterpenoid

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Magoichi Sako, Hikokazu Suzuki, Noriyuki Yamamoto, Kosaku Hirota and Yoshifumi Maki


Abstract

Selective O-deacylations of taxinine 1a, readily available from needles of Taxus cuspidata, at C-2, C-5 and C-9,10 have been accomplished by treatment with barium hydroxide octahydrate, sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al®[hair space]) or diisobutylaluminium hydride (DIBAL-H) under mild conditions to give 2,9,10-tri-O-deacetyltaxinine 4b, 2-O-deacetyltaxinine 4c, 5-O-decinnamoyltaxinine (taxinine A, 5a) and 2,5-di-O-deacyltaxinine (taxuspine G, 5b), respectively, which are expected to be useful synthetic intermediates for biologically active taxinine derivatives.


References

  1. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon and A. T. McPhail, J. Am. Chem. Soc., 1971, 93, 2325 CrossRef.
  2. F. Gueritte-Voegelein, L. Mangatal, D. Guenard, P. Potier, J. Guilhem, M. Cesario and C. Pascard, Acta Crystallogr., Sect. C, 1990, 46, 781 CrossRef; D. Geunard, F. Gueritte-Voegelein and P. Potier, Acc. Chem. Res., 1993, 26, 160 CrossRef CAS.
  3. D. G. I. Kingston, A. A. Molinero and J. M. Rimoldi, in Progress in the Chemistry of Organic Natural Products, 61, ed. W. Herz, G. W. Kirby, R. E. Moore, W. Steglich and Ch. Tamm, Springer-Verlag, New York, 1993, p. 160 Search PubMed; V. Farina, in The Chemistry and Pharmacology of Taxol® and Its Derivatives(Pharmacochemistry Library, Vol. 22, ed. H. Timmerman), Elsevier, Amsterdam, 1995 Search PubMed; Taxane Anticancer Agents: Basic Science and Current Status, ed. G. I. Georg, T. T. Chen, I. Ojima and D. M. Vyas, American Chemical Society, Washington, DC, 1995 Search PubMed.
  4. H. G. Meerpohl, A. du Bois, H. Kuhnle, H. J. Luck, R. Kreienberg, V. Mobus, T. Bauknecht, O. Kochli, H. Bochtler and K. Diergarten, Semin. Oncol., 1995, 22, 7 CAS; R. F. Ozols, Ann. Med., 1995, 27, 127 Search PubMed.
  5. J. M. Nabholtz, K. Gelmon, M. Bontenbal, M. Spielmann, G. Catimel, P. Conte, U. Klaassen, M. Namer, J. Bonneterre, P. Fumoleau and B. Winograd, J. Clin. Oncol., 1996, 14, 1858 Search PubMed; G. W. Sledge Jr., Semin. Oncol., 1996, 23, 10 CAS.
  6. P. C. Hoffman, G. A. Masters, L. C. Drinkard, S. A. Krauss, B. L. Samuels, H. M. Golomb and E. E. Vokes, Ann. Oncol., 1996, 7, 314 CAS; B. E. Hillner, J. Natl. Cancer Inst. Monogr., 1995, 65 Search PubMed.
  7. F. H. Cortes and J. Aisner, Semin. Oncol., 1997, 24, S2–51; A. A. Forastiere, Ann. Oncol., 1994, 5, Suppl. 6, S51; A. A. Forastiere, D. Neuberg, S. G. Taylor 4th, R. DeConti and G. Adams, J. Natl. Cancer Inst. Monogr., 1993, 181 Search PubMed.
  8. S. G. Arbuck and B. A. Blaylock, in Taxol®: Science and Applications, ed. M. Suffness, CRC Press, Boca Raton, FL. 1995, p. 379 Search PubMed; I. Ojima, J. C. Slater, S. D. Kuduk, C. S. Takeuchi, R. H. Gimi, C.-M. Sun, Y. H. Park, P. Pera, J. M. Veith and R. J. Bernacki, J. Med Chem., 1997, 40, 267 Search PubMed; I. Ojima, S. D. Kuduk, P. Pera, J. M. Veith and R. J. Bernacki, J. Med. Chem., 1997, 40, 279 CrossRef CAS.
  9. G. Appendino, P. Gariboldi, A. Pisetta, E. Bombardelli and B. Gabetta, Phytochemistry, 1992, 31, 4253 CrossRef CAS.
  10. J. Kobayashi, H. Hosoyama, H. Shigemori, Y. Koiso and S. Iwasaki, Experientia, 1995, 51, 592 Search PubMed.
  11. G. Chauviere, D. Guenard, F. Picot, V. Senilh and P. Potier, C. R. Hebd. Seances Acad. Sci., Ser. 2, 1981, 293, 501 Search PubMed; G. Chauviere, D. Guenard, C. Pascard, F. Picot, P. Potier and T. Prange, J. Chem. Soc., Chem. Commun., 1982, 495 RSC; F. Yoshizaki, M. Fukuda, S. Hisamichi, T. Ishida and Y. In, Chem. Pharm. Bull., 1988, 36, 2098 CAS; Z.-P. Zhang, Z.-J. Jia, Z.-Q. Zhu, Y.-X. Cui, J.-L. Cheng and Q.-G. Wang, Chin. Sci. Bull., 1989, 21, 1630 Search PubMed; Planta Med., 1990, 56, 293 Search PubMed.
  12. J. Kobayashi, H. Hosoyama, X.-X. Wang, H. Shigemori, Y. Koiso, S. Iwasaki, T. Sasaki, M. Naito and T. Tsuruo, Bioorg. Med. Chem. Lett., 1996, 7, 393 CrossRef.
  13. (a) H. Kondo and T. Takahashi, Yakugaku Zasshi, 1925, 45, 861; (b) D. H. Eyre, J. W. Harrison, R. M. Scrowston and B. Lythgoe, Proc. Chem. Soc., London, 1963, 271 RSC; (c) Y. Maki and M. Sako, J. Synth. Org. Chem. Jpn., 1993, 51, 298 Search PubMed and references cited therein.
  14. (a) X.-J. Tong, W.-S. Fang, J.-Y. Zhou, C.-H. He, W.-M. Chen and Q.-C. Fang, Yaoxue Xuebao, 1994, 29, 55 (Chem. Abstr., 1994, 121, 31107) Search PubMed; (b) X.-J. Tong, Y.-C. Liu and C.-J. Chang, Nat. Prod. Lett., 1995, 6, 197 (Chem. Abstr., 1996, 125, 190577) Search PubMed.
  15. From Taxus baccata: (a) J. N. Baxter, B. Lythgoe, B. Scales, R. M. Scrowston and S. Trippett, J. Chem. Soc., 1962, 2964 RSC; (b) M. Dukes, D. H. Eyre, J. W. Harrison, R. M. Scrowston and B. Lythgoe, J. Chem. Soc. C, 1967, 448 RSC; (c) M. Kurono, Y. Nakadaira, S. Onuma, K. Sasaki and K. Nakanishi, Tetrahedron Lett., 1963, 2153 CrossRef CAS; (d) L. H. D. Jenniskens, E. L. M. van Rozendaal, T. A. van Beek, P. H. G. Wiegerinck and H. W. Scheeren, J. Nat. Prod., 1996, 59, 117 CrossRef CAS.
  16. From Taxus cuspidata: (a) H. C. Chiang, M. C. Woods, Y. Nakadaira and K. Nakanishi, Chem. Commun., 1967, 1201 RSC; (b) M. C. Woods, H.-C. Chiang, Y. Nakadaira and K. Nakanishi, J. Am. Chem. Soc., 1968, 90, 522 CrossRef CAS; (c) F. Yashizaki, R. Yanagihashi and S. Hisamichi, Shoyakugaku Zasshi, 1988, 42, 151 (Chem. Abstr., 1989, 110, 72055) Search PubMed; (d) Y. Konda, T. Sasaki, X.-L. Sun, X. Li, M. Onda, H. Takayanagi and Y. Harigaya, Chem. Pharm. Bull., 1994, 42, 2621 CAS; (e) J. Kobayashi, A. Ogiwara, H. Hosoyama, H. Shigemori, N. Yoshida, T. Sasaki, Y. Li, S. Iwasaki, M. Naito and T. Tsuruo, Tetrahedron, 1994, 50, 7401 CrossRef CAS.
  17. From Taxus chinensis(1×10–3%): H.-C. Chiang, Shih Ta Hsueh Pao, 1975, 20, 147 (Chem. Abstr., 1976, 84, 118448) Search PubMed.
  18. From Taxus cuspidata: F. Yoshizaki, N. Takahashi and S. Hisamichi, Annu. Rep. Tohoku Coll. Pharm., 1987, 34, 187 (Chem. Abstr., 1989, 110, 121510) Search PubMed.
  19. From Taxus cuspidata: F. Yoshizaki, M. Madarame, C. Takahashi and S. Hisamichi, Shoyakugaku Zasshi, 1986, 40, 429 (Chem. Abstr., 1987, 107, 130861) Search PubMed; F. Yoshizaki, M. Fukuda and S. Hisamichi, Annu. Rep. Tohoku Coll. Pharm., 1987, 34, 111 (Chem. Abstr., 1989, 110, 21128) Search PubMed.
  20. X.-J. Tong, W.-S. Fang, J.-Y. Zhou, C.-H. He, W.-M. Chen and Q.-C. Fang, Chin. Chem. Lett., 1993, 4, 887 (Chem. Abstr., 1994, 121, 31087) CAS.
  21. From Taxus cuspidata: S. Tachibana, A. Matsuo, K. Itoh and T. Oki, Mokuzai Gakkaishi, 1994, 40, 1008 (Chem. Abstr., 1995, 123, 86266) Search PubMed.
  22. From Taxus mairei: (4.0×10–4%): C.-L. Liu, Y.-C. Lin, Y.-M. Lin and F.-C. Chen, Taiwan Ko Hsueh, 1984, 38, 119 (Chem. Abstr., 1985, 103, 165998) Search PubMed.
  23. M. Shiro, T. Sato, H. Koyama, Y. Maki, K. Nakanishi and S. Uyeo, Chem. Commun., 1966, 97 Search PubMed; M. Shiro and H. Koyama, J. Chem. Soc. B, 1971, 1342 RSC.
  24. H. Morita, L. Wei, A. Gonda, K. Takeya, H. Itokawa, H. Fukaya, H. Shigemori and J. Kobayashi, Tetrahedron, 1997, 53, 4621 CrossRef CAS.
  25. S. Uyeo, K. Ueda, Y. Yamamoto and Y. Maki, Yakugaku Zasshi, 1964, 84, 762 CAS.
  26. P. H. G. Wiegerinck, L. Fluks, J. B. Hammink, S. J. E. Mulders, F. M. H. de Groot, H. L. M. van Rozendaal and H. W. Scheeren, J. Org. Chem., 1996, 61, 7092 CrossRef CAS.
  27. Y. Yamamoto, S. Uyeo and K. Ueda, Chem. Pharm. Bull., 1969, 3, 386.
  28. S. Uyeo, K. Ueda, Y. Yamamoto and Y. Maki, Yakugaku Zasshi, 1965, 85, 404 CAS.
  29. N. Wu, L. Yang, Q.-T. Zheng, W.-S. Fang, X.-J. Tong, Q.-C. Fang, D.-D. Wu, F. Xue and T. C. W. Mak, Jiegou Huaxue, 1996, 15, 387 (Chem. Abstr., 1996, 125, 270502) Search PubMed.
  30. Y. Bathini, R. G. Micetich and M. Daneshtalab, Synth. Commun., 1994, 24, 1513 CAS.
  31. (a) J. Kobayashi, A. Inubushi, H. Hosoyama, N. Yoshida, T. Sasaki and H. Shigemori, Tetrahedron, 1995, 51, 5971 CrossRef CAS (3.4 × 10–4% from stems); (b) X.-J. Tong, W.-S. Fang, J.-Y. Zhou, C.-H. He, W.-M. Chen and Q.-C. Fang, J. Nat Prod., 1995, 58, 233 CrossRef CAS.
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