Chemoenzymatic total synthesis of the sesquiterpene (–)-patchoulenone

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Martin Banwell and Malcolm McLeod


Abstract

Monochiral cis-1,2-dihydrocatechol 2, obtained by microbial oxidation of toluene, has been converted, via intermediate 3, into the cyperene-type sesquiterpene 1.


References

  1. B. Trivedi, O. Motl, V. Herout and F. Sorm, Collect. Czech. Chem. Commun., 1964, 29, 1675 CAS.
  2. C. Thebtaranonth, Y. Thebtaranonth, S. Wanauppathamkul and Y. Yuthavong, Phytochemistry, 1995, 40, 125 CrossRef CAS.
  3. A. Hisham, V. Wray, L. Pieters, M. Claeys, R. Dommisse and A. Vlietinck, Magn. Reson. Chem., 1992, 30, 295 CAS.
  4. H. Achenbach and A. Schwinn, Phytochemistry, 1995, 38, 1037 CrossRef CAS.
  5. G. Büchi, W. D. MacLeod Jr. and J. Padilla O., J. Am. Chem. Soc., 1964, 86, 4438 CrossRef and refererences cited therein.
  6. H. Hikino, K. Ito, K. Aota and T. Takemoto, Chem. Pharm. Bull., 1968, 16, 43 CAS.
  7. W. F. Erman and L. C. Stone, J. Am. Chem. Soc., 1971, 93, 2821 CrossRef CAS.
  8. For reviews on the applications of cis-1,2-dihydrocatechols in synthesis see: D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 8, 3 Search PubMed; H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795 Search PubMed; S. M. Brown, and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT, 1993, vol. 2, 113 CrossRef CAS; T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT, 1995, vol. 1, p. 271 CrossRef CAS; T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993 CrossRef CAS.
  9. M. G. Banwell, P. Darmos, D. C. R. Hockless and M. D. McLeod, Synlett., 1998, 897 CAS.
  10. R. A. Holton and A. D. Williams, J. Org. Chem., 1988, 53, 5981 CrossRef CAS.
  11. G. A. Molander and C. Kenny, J. Am. Chem. Soc., 1989, 111, 8236 CrossRef CAS and references cited therein.
  12. H. O. House, C.-Y. Chu, J. M. Wilkins and M. J. Umen, J. Org. Chem., 1975, 40, 1460 CrossRef CAS.
  13. T. L. Fevig, R. L. Elliott and D. P. Curran, J. Am. Chem. Soc., 1988, 110, 5064 CrossRef CAS; I. Fleming and I. Paterson, Synthesis, 1979, 736 CrossRef CAS.
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