One step transformation of tricyclopentabenzene (trindane) [C15H18] to 4-[1R,2S,4R,5S)-1,2,5-trihydroxy-3-oxabicyclo[3.3.0]octane-4 spiro-1′-(2′-oxocyclopentan)-2-yl]butanoic acid [C15H22O7]

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Subramania Ranganathan, K. M. Muraleedharan, Parimal Bharadwaj and K. P. Madhusudanan


Abstract

The complete, Ru(VIII) mediated oxidation of the benzene ring of trindane 1 is contained within the framework of peripheral methylenes to yield the unfragmented product 2.


References

  1. R. Mayer, Chem. Ber., 1956, 89, 1443 CAS; F. Petru and V. Galik, Chem. Listy, 1957, 51, 2371 Search PubMed.
  2. T. J. Katz and W. Slusarek, J. Am. Chem. Soc., 1980, 102, 1058 CrossRef CAS.
  3. P. Braquet, Ginkgolides-Chemistry, Biology, Pharmacology and Clinical Perspectives, J. R. Prous Science Publishers, Barcelona, 1988, vol. 1, p. xv Search PubMed; E. J. Corey and A. Y. Gavai, Tetrahedron Lett., 1989, 30, 6959 Search PubMed; E. J. Corey, M.-C. Kang, M. C. Desai, A. K. Ghosh and I. N. Houpis, J. Am. Chem. Soc., 1988, 110, 649 CrossRef CAS; D. Luca and P. Magnus, J. Chem. Soc., Perkin Trans. 1, 1991, 2661 CrossRef CAS.