First Synthesis of (+)-5α-Hydroxy-β-selinene and (–)-5β-Hydroxy-β-selinene

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Zhaoming Xiong, Gang Zhou, Yonggang Chen and Yulin Li


Abstract

A facile and efficient synthesis of (+)-5α-hydroxy-β-selinene 1 and (–)-5β-hydroxy-β-selinene 2 starting from (+)-dihydrocarvone has been carried out.


References

  1. T. A. Van Beek and A. De Grot, Recl. Trav. Chim. Pays-Bas, 1986, 105, 513 CAS.
  2. V. J. Paul, J. M. Crown and J. H. Cardellina II, J. Chem. Ecol., 1993, 19, 1847 Search PubMed.
  3. M. Ando, K. Isogai, H. Azami, N. Hirata and Y. Yanagi, J. Nat. Prod., 1991, 54, 1017 CrossRef CAS.
  4. J. Jakupovic, L. Lehmann, F. Bohlmann, R. M. King and H. Robinson, Phytochemistry, 1988, 27, 3831 CrossRef CAS.
  5. Z. M. Xiong, J. Yang and Y. L. Li, Tetrahedron Asymmetry, 1996, 7, 2607 CrossRef.
  6. (a) For reviews of the deoxygenation of carbonyl compounds, see S. Yamamura and S. Nishiyama, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 8, p. 307 Search PubMed; (b) R. O. Hutchins and M. K. Hutchins, Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, vol. 8, p. 327 Search PubMed.
  7. J. H. Brewster and H. O. Bayer, J. Org. Chem., 1964, 29, 105; 116 CAS.
  8. For a review of the epoxidation of alkenes, see A. S. Rao, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 7, p. 357 Search PubMed.
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