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大学・研究所にある論文を検索できる 「Synthetic Studies toward Tubiferal A」の論文概要。リケラボ論文検索は、全国の大学リポジトリにある学位論文・教授論文を一括検索できる論文検索サービスです。

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Synthetic Studies toward Tubiferal A

Yukutake, Yuki 北海道大学

2022.03.24

概要

Many natural organic compounds found in nature exhibit a wide range of biological activities and have long been used as pharmaceuticals, agrochemicals, and useful lead compounds for these purposes. A variety of natural chemical scaffolds, such as terpenes, alkaloids, polyethers, peptides are known as biologically active compounds. In terms of terpenes, Taxol, a diterpenoid isolated from the bark of Taxus brevifolia, has been used as a new drug for antineoplastic activity.1) Solanoeclepin A,2) a terpenoid isolated from the hydroponic solution of potato in 1986, is expected to be a natural pesticide because of its remarkable hatching-promoting activity against potato cyst nematodes. On the other hand, alkaloids also exhibit a wide range of biological activities. Strychnine is an indole alkaloid first discovered from Strychnos ignatia in 1818. Although it is no longer used in medicine due to its extremely high toxicity, it had been used in medicine as a convulsant inducing drug and ghrelin receptor antagonist.3) Morphine is an opium alkaloid found from the Opinium poppy Papaver Somniferum, and has strong analgesic and anesthetic properties.4) In polyether, halichondrin B, a huge molecule with molecular weight of over 1000 found from a marine sponge, Halichondria okadai, possesses a potent anticancer activity.5) Vancomycin, a cyclic peptide isolated from Streptomyces Orientalis, has a bactericidal effect on Gram-positive bacteria and bacteriostatic effect on enterococci. Vancomycin has such potent bioactivity that it has been called the last resort for infectious disease.6)

参考文献

1. (a) Wani, M. C.; Taylor, H. L.; Wall, M. E. J. Am. Chem. Soc. 1971, 93, 2325-2327. (b) Runowicz, C. D.; Wiernik, P. H.; Einzig, A. I.; Goldberg, G. L.; Horwitz, S, B. Cancer 1993, 71, 1591-1596.

2. Tanino, K.; Takahashi, M.; Tomata, Y.; Tokura, H.; Uehara, T.; Narabu, T.; Miyashita, M. Nat. Chem. 2011, 3, 484-488.

3. Munro, J. M. H. Br. Med. J. 1914, 1, 854-856.

4. Herbert, R. B.; Venter, H.; Pos, S. Nat. Prod. Rep. 2000, 17, 317-322.

5. Hirata,Y.; Uemura, D. Pure Appl. Chem. 1986, 58, 701-710.

6. (a) McCormick M. H.; Mcguire, J. M.; Pittenger G. E.; Stark, W. M. Antibiot. Annu. 1995-56, 606. (b) Evans, D. E.; Wood, M. R.; Trotter, W.; Richardson, T. I.; Barrow, J. C.; Kattz, J. L. Angew. Chem. Int. Ed. 1998, 37, 2700-2704.

7. (a) Thimmappa, R.; Gleisler, K.; Louveau, T.; O’Maille, P.; Osbourn, A. Annu. Rev. Plant Biol., 2014, 65, 225-227. (b) Xu, R.; Fazio, G. C.; Matsuda, S. P. T. Phytochemistry 2004, 65, 261-291.

8. Shi, Q-Q.; Wang, W.-H.; Lu, J.; Li, D.-S.; Xhou, L.; Qui, M.-H. Planta, Med. 2019, 85, 154-159.

9. Zhang, L.-S.; Wang, Y.-L.; Liu, Q.; Zhou, C.-X.; Mo, J.-X.; Lin, L.-G.; Gan, L-S. Phytochem. Lett. 2018, 23, 172-175.

10. Kamata, K.; Onuki, H.; Hirota, H.; Yamamoto, Y.; Hayashi, M.; Komiyama, K.; Sato, M.; Ishibashi, M. Tetrahedron 2004, 60, 9835-9839.

11. Wang, X. Enolization regioselectivity involving stereoisomeric 4a-methyl-5-methoxy- perhydrobenzo[7]annulen-2-ones. Studies toward the enantioselective synthesis of tubiferal A. 2010, Doctoral dissertation, Ohio State University.

12. Hiramatsu, T. Studies toward the enantioselective total synthesis of tubiferal A. 2014, Doctoral dissertation, Hokkaido University.

13. Hiersemann, M; Nubbemeyer, U. (2007) The Claisen Rearrangement. Wiley-VCH: Weinheim.

14. Kotoku, N.; Sumii, Y.; Kobayashi, M. Org. Lett. 2011, 13, 3514-3517.

15. (a) Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451-2458. (b) Determination of the enantiomeric ratios of alcohol (S)-1.14 and allylboronate (S)- and (R)-1.10. Scheme S1. Determination of enantiomeric purity of alcohol (S)-1.12 and allylborane (R)- and (S)-1.8.

16. Ito, H.; Miya, T.; Sawamura, M Tetrahedron 2012, 68, 3423-3427.

17. (a) Nagao, K.; Yokobori, U.; Makida, Y.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2012, 134, 8982-8987. (b) Ohmiya, H.; Sawamura, M. Bull. Chem. Soc. Jpn. 2021, 94, 197-203.

18. Yamada, T, Yoshimura, F, Tanino, K. Tetrahedron Lett. 2013, 54, 522-525.

19. (a) Ohira, S. Synth. Commun, 1989, 19, 561-564. (b)Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett, 1996, 521-522.

20. Ohmori, K.; Nishiyama, S.; Yamamura, S Tetrahedron Lett. 1995, 36, 6519-6522.

21. Schultz, A. G.; McCloskey, P. J. J. Org. Chem. 1985, 50, 5905-5907.

22. Zhao, Y.; Snieckus, V. Org. Lett. 2014, 16, 390-393.

23. Mori, N. Togo, H. Synlett, 2005, 9, 1456-1458

24. Appel, R.; Schöler, H. Chem. Ber. 1977, 110, 2382-2384.

25. A small amount of each diastereomer in pure form was obtained through incomplete separation of the isomeric mixture of 1.33 by silica gel chromatography. Upon treatment with mCPBA, the major isomer of 1.33 was selectively converted to epoxide 1.34a, and the minor diastereomer of 1.33 afforded a mixture of epoxides 1.34b and 1.34c. Since the stereochemistry of 1.34c was determined by X-ray crystallography (see below), the author could assign the configuration of epoxide 1.34b having the same AB ring moiety with 1.34c. The configuration of epoxide 1.34a was expected by assuming the oxidation of the major isomer of 1.33 from the convex face.

26. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794-3796.

27. Hill, R. R.; Rychnovsky S.D. J. Org. Chem. 2016, 81, 10707-10714.

28. (a) Ge, Y. Cui, X-Y., Tan, S.M., Jiang, T. H., Ren, J., Lee, N., Lee, R., Tan, C.-H. Angew. Chem. Int. Ed. 2019, 58, 2382-2386. (b) Takenouchi, Y., Kojima, R., Momma, R., Ito, H. Synlett, 2017, 28, 270-274

29. (a) Hoffmann, R. W.; Zeiss, H.-J. Angew. Chem. Int. Ed. Engl. 1979, 18, 306-307. (b) Hoffmann, R. W.; Zeiss, H.-J. J. Org. Chem. 1981, 46, 1309-1314.

30. Wuts, P. G. M., Thompson, P. A.; Callen, G. R. J. Org. Chem. 1983, 48, 5398-5400.

31. Knochel, P. J. Am. Chem. Soc. 1990, 112, 7431-7433.

32. (a) Yoshimura, F.; Itoh, R.; Torizuka, M.; Mori, G.; Tanino, K. Angew. Chem, Int. Ed. 2018, 57, 17161-17167. (b) Yoshimura, F.; Torizuka, M.; Mori, G.; Tanino, K. Synlett 2012, 23, 251- 254.

33. Fujii, T.; Orimoto, K.; Nakada, M. Tetrahedron Lett. 2014, 55, 1100-1103.

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