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DOI: 10.1039/A603209E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 317-322

Total syntheses of (+)-asperlin, (+)-acetylphomalactone and (5S,6S,7R,8S)-asperlin based on the kinetic resolution of 2-furylmethanols

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Zhi-Cai Yang, Xiao-Bin Jiang, Zhi-Min Wang and Wei-Shan Zhou

Abstract

The total syntheses of (+)-asperlin 1, (+)-acetylphomalactone 2 and (5S,6S,7R,8S)-asperlin 3 have been achieved employing the kinetic resolution of unsymmetric divinylmethanol using modified Sharpless reagents, which produced two oxidation products, as a key step.

References

  1. (a) A. D. Argoudelis, J. H. Coats and R. R. Herr, Antimicrob. Agents Chemother., 1965, 801 CAS; (b) S. P. Owen and B. K. Bhuyan, Antimicrob. Agents Chemother., 1965, 804 CAS; (c) A. D. Argoudelis and J. F. Zieserl, Tetrahedron Lett., 1966, 1969 CrossRef.
  2. S. Mizuba, K. Lee and J. Liu, Can. J. Microbiol, 1975, 21, 1781 CAS.
  3. (a) S. Ramesh and R. W. Franck, Tetrahedron: Asymmetry, 1990, 1, 137 CrossRef CAS; (b) Y. Masaki, T. Imaeda, H. Oda, A. Itoh and M. Shiro, Chem. Lett., 1992, 1209 CAS; (c) T. Murayama, T. Sugiyama and K. Yamashita, Agric. Biol. Chem., 1986, 50, 1923 CAS; (d) T. Murayama, T. Sugiyama and K. Yamashita, Agric. Biol. Chem., 1987, 51, 2055 CAS; (e) T. K. M. Shing and M. Aloui, J. Chem. Soc., Chem. Commun., 1988, 1525 RSC; Can. J. Chem., 1990, 68, 1035 Search PubMed; (f) S. Lesage and A. S. Perlin, Can. J. Chem., 1978, 56, 2889 CAS; (g) H. Hiraoka, K. Furuta, N. Ikeda and K. Yamamoto, Bull. Chem. Soc. Jpn., 1984, 57, 2777 CAS.
  4. Syntheses of 2: (a) S. Lesage and A. S. Perlin, Can. J. Chem., 1978, 56, 2889 CAS; (b) T. Murayama, T. Sugiyama and K. Yamashita, Agric. Biol. Chem., 1987, 51, 2055 CAS; (c) T. Honda, T. Kametani, K. Kanai, Y. Tatsuzaki and M. Tsubuki, J. Chem. Soc., Perkin Trans. 1, 1990, 1733 RSC.
  5. Syntheses of 3: (a) S. Lesage and A. S. Perlin, Can. J. Chem., 1978, 56, 2889 CAS; (b) See ref. 4b.
  6. T. Honda, N. Sano and K. Kanai, Heterocycles, 1995, 41, 425 CAS.
  7. Z.-C. Yang and W.-S. Zhou, Tetrahedron Lett., 1995, 36, 5617 CrossRef CAS.
  8. W.-S. Zhou, Z.-H. Lu and Z.-M. Wang, Tetrahedron Lett., 1991, 32, 1467 CrossRef CAS.
  9. (a) S. L. Schreiber, T. S. Schreiber and D. B. Smith, J. Am. Chem. Soc., 1987, 109, 1525 CrossRef CAS; (b) S. Hatakeyama, K. Sakurai and S. Takano, J. Chem. Soc., Chem. Commun., 1985, 1759 RSC; (c) B. Hafele, D. Schroter and V. Jager, Angew. Chem., Int. Ed. Engl., 1986, 25, 87 CrossRef.
  10. Z.-C. Yang, X.-B. Jiang, Z.-M. Wang and W.-S. Zhou, J. Chem. Soc., Chem. Commun., 1995, 2389 RSC.
  11. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092 CrossRef CAS.
  12. R. H. Evans, Jr., G. A. Ellestad and M. P. Kunstmwnn, Tetrahedron Lett., 1969, 1791 CrossRef.
  13. S. Mizuba, K. Lee and J. Jiu, Can. J. Microbiol., 1975, 21, 1781 CAS.
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