Simple synthesis of enantiomers of 6-hydroxyalkan-4-olides by stereoselective hydrogenation of methyl 4,6-dioxoalkanoates

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

Stefan Schulz


Abstract

A simple method for the synthesis of (S,S)- or (R,R)-6-hydroxyalkan-4-olides, components of the pheromonal secretion of the butterfly Idea leuconoe, in high ee by enantioselective hydrogenation of 4,6-diketo esters with a commercial available Ru–BINAP catalyst is described.


References

  1. S. Schulz and R. Nishida, Bioorg. Med. Chem., 1996, 4, 341 CrossRef CAS.
  2. R. Nishida, S. Schulz, C. H. Kim, H. Fukami, Y. Kuwahara, K. Honda and N. Hayashi, J. Chem. Ecol., 1996, 22, 949 Search PubMed.
  3. M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Komobayashi, S. Akutagawa, T. Ohta, H. Takaya and R. Noyori, J. Am. Chem. Soc., 1988, 110, 629 CrossRef CAS.
  4. H. Kawano, Y. Ishii, M. Saburi and Y. Uchida, J. Chem. Soc., Chem. Commun., 1988, 35, 87 RSC.
  5. L. Shao, H. Kawano, M. Saburi and Y. Uchida, Tetrahedron, 1993, 49, 1997 CrossRef CAS.
  6. D. J. Ager and S. A. Laneman, Tetrahedron: Asymmetry, 1997, 8, 3327 CrossRef CAS.
  7. K. Mashima, K. Kusano, M. Sato, Y. Matsumura, K. Nozaki, H. Komobayashi, N. Sayo, Y. Hori, T. Ishizaki, S. Akutagawa, H. O. T. Takaya and R. Noyori, J. Org. Chem., 1994, 59, 3064 CrossRef CAS.
  8. T. Eguchi, K. Arakawa, T. Terachi and K. Kakinuma, J. Org. Chem., 1997, 62, 1924 CrossRef CAS.
  9. A. Hefetz, T. Taghizadeh and W. Francke, Z. Naturforsch., 1996, 51c, 409 Search PubMed.
  10. C. R. Holmquist and E. J. Roskamp, J. Org. Chem., 1989, 54, 3258 CrossRef CAS.
  11. A. P. Krapcho, Synthesis, 1982, 893 CrossRef.
  12. U. S. Racherla and H. C. Brown, J. Org. Chem., 1991, 56, 401 CrossRef CAS.
  13. M. J. Rozema, A. Sidduri and P. Knochel, J. Org. Chem., 1992, 57, 1956 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.