Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Absolute Stereochemistry Determination of Tetrin B

  • Published : 2002.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

The absolute stereochemistry of tetrin B (1), an antifungal antibiotic isolated from a soil actinomycete was determined by applying Rychnovsky analysis, the modified Mosher method, and CD exciton chirality to be 4R, 5R, 7S, 9R, 11S, 12R, 13S, 15R, 24S, and 25R.

Keywords

References

  1. Rinehart, K. L., Jr.; German, V. F.; Tucker, W. P.; Gottlieb, D. Justus Liebigs Ann. Chem. 1963, 668, 77. https://doi.org/10.1002/jlac.19636680108
  2. Rinehart, K. L., Jr.; Tucker, W. P.; Pandey, R. C. J. Am. Chem. Soc. 1971, 93, 3747. https://doi.org/10.1021/ja00744a031
  3. Pandey, R. C.; Rinehart, K. L., Jr. J. Antibiotics 1977, 30, 158. https://doi.org/10.7164/antibiotics.30.158
  4. Patrick, J. B.; Williams, R. R.; Wolf, C. F.; Weeb, J. S. J. Am. Chem. Soc. 1958, 80, 6688. https://doi.org/10.1021/ja01557a059
  5. Dornberger, K.; Thrum, H.; Radics, L. Tetrahedron 1979, 35, 1851. https://doi.org/10.1016/0040-4020(79)80009-5
  6. Ceder, O.; Hansson, B.; Rapp, U. Tetrahedron 1977, 33, 2703. https://doi.org/10.1016/0040-4020(77)80294-9
  7. Oppong, L.; Pauls, H. W.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1986, 1241.
  8. Duplantier, A. J.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7079. https://doi.org/10.1021/ja00175a063
  9. Lancelin, J. M.; Beau, J. M. J. Amer. Chem. Soc. 1990, 112, 4060. https://doi.org/10.1021/ja00166a065
  10. Lancelin, J. M.; Beau, J. M. Bull. Soc. Chim. Fr. 1995, 132, 215.
  11. Ryu, G.; Choi, W.-C.; Hwang, S.; Yeo, W.-H.; Lee, C.-S.; Kim, S.-K. J. Nat. Prod. 1999, 62, 917. https://doi.org/10.1021/np9805645
  12. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. https://doi.org/10.1016/S0040-4039(00)94399-5
  13. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. https://doi.org/10.1021/jo00065a011
  14. Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099. https://doi.org/10.1016/S0040-4039(00)97250-2
  15. Chuvhe, J.; Dana, G.; Monot, M. R. Bull. Soc. Chim. Soc. 1976, 9, 3300.
  16. Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 95, 512.
  17. Ohtani, I.; Kusumi, T.; Kahman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 73, 4092.
  18. Kusumi, T.; Fukushima, T.; Ohtami, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939.
  19. Dornberger, K.; Thrum, H.; Radics, L. Tetrahedron 1979, 35, 1851. https://doi.org/10.1016/0040-4020(79)80009-5
  20. Radics, L.; Incze, M.; Dornberger, K.; Thrum, H. Tetrahedron 1982, 38, 183. https://doi.org/10.1016/0040-4020(82)85064-3

Cited by

  1. Non-isoprenoid polyene natural products – structures and synthetic strategies vol.12, pp.40, 2014, https://doi.org/10.1039/C4OB01337A
  2. Two New Furanocoumarins from the Roots of Angelica dahurica vol.24, pp.11, 2002, https://doi.org/10.5012/bkcs.2003.24.11.1699
  3. Absolute Stereochemistry Determination of Tetrin B. vol.34, pp.12, 2002, https://doi.org/10.1002/chin.200312197
  4. Diarylheptanoids from the Roots of Juglans mandshurica vol.25, pp.3, 2002, https://doi.org/10.5012/bkcs.2004.25.3.397
  5. Glycosylated Methoxy-Macrolactins from a Marine Sediment Bacterium Bacillus subtilis vol.87, pp.2, 2002, https://doi.org/10.3987/com-12-12594
  6. Enantioselective Modular Total Synthesis of Macrolides Sch725674 and C‐4‐epi‐Sch725674 vol.2016, pp.6, 2002, https://doi.org/10.1002/ejoc.201501531