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

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1997, Pages 317-321

  Yang, Zhi Cai ^a   Jiang, Xiao Bin ^a,b   Wang, Zhi Min ^a   Zhou, Wei Shan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748551063     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a603209e     Document Type: Article

References (27)

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