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Total Synthesis of Dihydroreynosin and Dihydrosantamarine via Tandem Cope-Claisen Rearrangement

  • Ki-Whan Chi (Department of Chemistry, University of Ulsan) ;
  • Stanley Raucher (Department of Chemistry, University of Washington)
  • Published : 1991.04.20

Abstract

The total synthesis of dihydroreynosin (1) and dihydrosantamarine (2) via tandem Cope-Claisen rearrangement has been accomplished starting from (S)-carvone (4).

Keywords

References

  1. Fortschr. Chem. Org. Naturst. v.38 N. H. Fischer;E. J. Olivier;H. D. Fischer
  2. The Total Synthesis of Natural Products v.5 J. ApSimon
  3. J. Org. Chem. v.51 S. Raucher;K.-W. Chi;K. -J. Hwang;J. E. Burks, Jr.
  4. Chem. Rev. v.88 F. E. Ziegler
  5. Phytochem. v.17 A. A. S. Rodrigues;M. Garcia;J. A. Rabi
  6. Tetrahedron v.21 A. Romo De Vivar;H. Jimenez
  7. Phytochem. v.9 H. Yoshioka;W. Renold;N. H. Fischer;A. Higo;T. J. Mabry
  8. J. Org. Chem. v.43 R. H. Mueller;J. G. Gillick
  9. Helv. Chim., Acta v.62 R. Baudat;M. Petrzilka
  10. J. Am. Chem. Soc. v.98 R. E. Ireland;R. H. Mueller;A. K. Willard
  11. Tetrahedron v.30 K. Takeda
  12. J. Org. Chem. v.51 W. J. Chazin;L. D. Colebrook
  13. Infrared Absorption Spectroscopy K. Nakanishi;P. H. Solomon
  14. J. Org. Chem. v.49 C. S. Wilcox;R. E. Babston
  15. J. Am. Chem. Soc. v.94 R. J. Arhart;J. C. Martin
  16. J. Am. Chem. Soc. v.106 D. A. Burnett;J. -K. Choi;Y. M. Tsai
  17. Phytochem. v.20 F. Bohlmann;R. K. Gupta;J. Jakupovic;R. M. King;H. Robinson
  18. Tetrahedron Lett. v.20 E. J. Corey;G. Schmidt
  19. Tetrahedron Lett. v.13 E. J. Corey;S. Terashima
  20. Phytochem. v.17 M. Ogura;G. A. Cordell;N. R. Farnsworth
  21. Tetrahedron Lett. K. Yamakawa;T. Tominaga;K. Nishitani
  22. Bull. Korean Chem. Soc. v.10 K. -W. Chi;S. Raucher

Cited by

  1. ChemInform Abstract: Total Synthesis of Dihydroreynosin and Dihydrosantamarine via Tandem Cope-Claisen Rearrangement. vol.22, pp.39, 1991, https://doi.org/10.1002/chin.199139218
  2. Effects of Solvents and Water in Ti(III)-Mediated Radical Cyclizations of Epoxygermacrolides. Straightforward Synthesis and Absolute Stereochemistry of (+)-3&agr;-Hydroxyreynosin and Related Eude vol.67, pp.8, 1991, https://doi.org/10.1021/jo016277e