Asymmetric hydrogen transfer protocol for enantiocontrolled synthesis of (–)-chokol G

(Note: The full text of this document is currently only available in the PDF Version )

Regina Mikie Kanada and Kunio Ogasawara


Abstract

An enantiocontrolled route to the (–)-chokol G, a fungitoxic metabolite from stromata of Epichloe typhia, has been devised by employing a RuII-catalyzed asymmetric hydrogen transfer reaction as the key step.


References

  1. S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya and R. Noyori, Angew. Chem., Int. Ed. Engl., 1997, 36, 288 CrossRef CAS Pertinent reviews, see: S. Hashiguchi, A. Fujii and R. Noyori, J. Synth. Org. Chem. Jpn., 1996, 54, 818 Search PubMed; R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97 Search PubMed.
  2. Isolation: H. Koshino, S. Togiya, S. Terada, T. Yoshihara, S. Sakamura, T. Shimanuki, T. Sato and A. Tajimi, Agric. Biol. Chem., 1989, 53, 789 Search PubMed.
  3. Only racemic syntheses have been reported so far: (a) N. Yamauchi and K. Kakinuma, Agric. Biol. Chem., 1989, 53, 3067 CAS; (b) S. Tanimori, T. Ohashi and M. Nakayama, Biosci. Biotechnol. Biochem., 1992, 56, 353; (c) L. Deloux and M. Srebnik, Tetrahedron Lett., 1996, 37, 2735 CrossRef CAS.
  4. R. D. Miller, D. L. Dolce and V. Y. Merritt, J. Org. Chem., 1976, 41, 1221 CrossRef CAS.
  5. J. Shimada, K. Hashimoto, B. H. Kim, E. Nakamura and I. Kuwajima, J. Am. Chem. Soc., 1984, 106, 1759 CrossRef CAS.
  6. S. N. Crane, T. J. Jenkins and D. J. Burnell, J. Org. Chem., 1997, 62, 8722 CrossRef CAS.
  7. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya and R. Noyori, Angew. Chem., Int. Ed. Engl., 1997, 36, 285 CrossRef CAS.
  8. An alternative chiral route to the enone 8: T. Sugahara and K. Ogasawara, Tetrahedron Lett., 1996, 37, 7403 Search PubMed.
  9. S. Okamoto, Y. Kobayashi, H. Kato, T. Takahashi, J. Tsuji and F. Sato, J. Org. Chem., 1988, 53, 5590 CrossRef CAS; I. Shiina, H. Iwadare, H. Sakoh, Y. Tani, M. Hasegawa, K. Saitoh and T. Mukaiyama, Chem. Lett., 1997, 1139 CAS; G. Stork, K. Manabe and L. Liu, J. Am. Chem. Soc., 1998, 120, 1337 CrossRef CAS.
  10. S. Takano, K. Inomata and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1992, 169 RSC.
  11. T. Imamoto, Y. Sugiura and N. Takiyama, Tetrahedron Lett., 1984, 25, 4233 CrossRef CAS.
  12. S. Tanimori, T. Ueda and M. Nakayama, Biosci. Biotechnol. Biochem., 1994, 58, 1174 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.