The first total synthesis of (±)-colabomycin D

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

Xudong Wei, J. J. Cronjé Grové and Richard J. K. Taylor


Abstract

The first total synthesis of a colabomycin antibiotic, colabomycin D, in racemic form, is reported. In addition, (±)-6′E-colabomycin A has been prepared and valuable spectroscopic information gained to confirm the structural assignment of colabomycin A.


References

  1. For a recent article giving lead references to all of the manumycin family see R. J. K. Taylor, L. Alcaraz, I. Kapfer-Eyer, G. Macdonald, X. Wei and N. J. Lewis, Synthesis, 1998, 775 Search PubMed.
  2. (a) L. Alcaraz, G. J. Macdonald, J. P. Ragot, N. Lewis and R. J. K. Taylor, J. Org. Chem, 1998, 63, 3526 CrossRef CAS; (b) L. Alcaraz, G. J. Macdonald, J. P. Ragot, N. Lewis and R. J. K. Taylor, Tetrahedron, 1999, 55, 3707 CrossRef.
  3. L. Alcaraz and R. J. K. Taylor, Chem. Commun., 1998, 1157 RSC.
  4. J. J. C. Grové, X. Wei and R. J. K. Taylor, Chem. Commun., 1999, 421 RSC.
  5. R. Grote, A. Zeeck, H. Drautz and H. Zähner, J. Antibiot., 1988, 41, 1178 CAS; R. Grote, A. Zeeck and J. M. Beale, J. Antibiot., 1988, 41, 1186 CAS.
  6. I. Sattler, PhD thesis, University of Göttingen, Germany, 1992(ref. 8 in I. Sattler, R. Thiericke and A. Zeeck, Nat. Prod. Rep., 1998, 15, 221) Search PubMed.
  7. G. Macdonald, L. Alcaraz, X. Wei, N. J. Lewis and R. J. K. Taylor, Tetrahedron, 1998, 54, 9823 CrossRef CAS.
  8. M. Miyashita, T. Suzuki, M. Hoshino and A. Yoshikoshi, Tetrahedron, 1997, 37, 12469 CrossRef CAS (see reference 12 therein for other methods of achieving this transformation).
  9. E. J. Corey and R. H. Wollenberg, J. Org. Chem., 1975, 40, 3788 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.