Synthesis of methyl secolonitoside

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

Richard T. Brown, Stephen P. Mayalarp and Joanne Watts


Abstract

The monoterpene diglycoside macrolide, lonitoside 1, is assumed to be biosynthesized via the intermediate acid secolonitoside 3 which has also been isolated from Lonicera nitida E. H. Wilson. We have synthesized the methyl ester of acid 3 from D-glucose, L-arabinose and (-)-citronellol [via methyl (E,S)-8-hydroxy-2,6-dimethyloct-2-enoate], both as a formal proof of structure and as an approach to a total synthesis of the macrolide 1.


References

  1. R. T. Brown, B. E. N. Dauda, M. Kandasamy and C. A. M. Santos, J. Chem. Soc., Perkin Trans. 1, 1991, 1539 RSC.
  2. T. Iwagawa and T. Haase, Phytochemistry, 1983, 22, 255 CrossRef CAS.
  3. R. T. Brown, N. E. Carter, K. W. Lumbard and F. Scheinmann, Tetrahedron Lett., 1995, 36, 8661 CrossRef CAS and references cited therein.
  4. R. R. Schmidt, Angew. Chem., Int. Ed. Engl., 1986, 25, 212 CrossRef.
  5. A. J. Ratcliffe, P. Konradson and B. Fraser-Reid, J. Am. Chem. Soc., 1990, 112, 5665 CrossRef CAS.
  6. D. D. Williams and W. L. Evans, Org. Synth., 1955, Coll. Vol. 3, p. 432.
  7. B. Helferich and H. Brederek, Justus Liebigs Ann. Chem., 1928, 465, 166 CAS.
  8. E. J. Corey, N. W. Gilman and B. E. Ganem, J. Am. Chem. Soc., 1968, 90, 5616 CrossRef CAS.
  9. D. D. Perrin, W. L. F. Armarego and D. R. Perrin, Purification of Laboratory Chemicals, Pergamon Press, Oxford, 1966 Search PubMed.
  10. K. C. Chan, R. A. Jewell, W. H. Nutting and H. Rapoport, J. Org. Chem., 1968, 33, 3382 CrossRef CAS.
  11. R. Schijf and W. Stevens, Recl. Trav. Chim. Pays-Bas, 1966, 85, 627 (Chem. Abstr., 1966, 65, 8754c) CAS.
Click here to see how this site uses Cookies. View our privacy policy here.