Enantiospecific total synthesis of (+)-2-pupukeanone

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

Adusumilli Srikrishna and Thumkunta Jagadeeswar Reddy


Abstract

The first total synthesis of chiral 2-pupukeanone (+)-4, starting from R-carvone (–)-7 employing a 5-exo-trig radical cyclisation as the key reaction for the construction of the tricyclic isotwistane carbon framework, is described.


References

  1. (a) B. J. Burreson, P. J. Scheuer, J. Finer and J. Clardy, J. Am. Chem. Soc., 1975, 97, 4763 CrossRef CAS; (b) M. R. Hagadone, B. J. Burreson, P. J. Scheuer, J. S. Finer and J. Clardy, Helv. Chim. Acta, 1979, 62, 2484 CrossRef.
  2. (a) E. J. Corey, M. Behforouz and M. Ishiguro, J. Am. Chem. Soc., 1979, 101, 1608 CrossRef CAS; (b) H. Yamamoto and H. L. Sham, J. Am. Chem. Soc., 1979, 101, 1609 CrossRef CAS; (c) G. A. Schiesher and J. D. White, J. Org. Chem., 1980, 45, 1864 CrossRef; (d) S. L. Hsieh, C. T. Chiu and N.-C. Chang, J. Org. Chem., 1989, 54, 3820 CrossRef For the synthesis of chiral analogue of 9-pupukeanone, see: A. Srikrishna, P. Hemamalini and G. V. R. Sharma, J. Org, Chem., 1993, 58, 2509 Search PubMed.
  3. (a) E. J. Corey and M. Ishiguro, Tetrahedron Lett., 1979, 2745 CrossRef CAS; (b) G. Frater and J. Wenger, Helv. Chem. Acta, 1984, 67, 1702 CrossRef CAS; (c) N.-C. Chang and C.-K. Chang, J. Org. Chem., 1996, 61, 4967 CrossRef CAS; (d) K. Kaliappan and G. S. R. Subba Rao, Tetrahedron Lett., 1997, 38, 2185 CrossRef CAS.
  4. A. Srikrishna, D. Vijaykumar and G. V. R. Sharma, Tetrahedron Lett., 1997, 38, 2003 CrossRef CAS.
  5. A. Srikrishna, G. V. R. Sharma, S. Danieldoss and P. Hemamalini, J. Chem. Soc., Perkin Trans. 1, 1996, 1305 RSC.
  6. J.-P. Gesson, J.-C. Jacquesy and B. Renoux, Tetrahedron, 1989, 45, 5853 CrossRef CAS.
  7. J. Rodriguez and J.-P. Dulcere, Synthesis, 1993, 1177 CrossRef CAS.
  8. In addition, varying amounts (15–20%) of easily separable 2,6-dimethyl-5-(2-acetoxy-1-bromoisopropyl)cyclohexenone, resulting from the trapping of the intermediate carbonium ion, was also obtained.
Click here to see how this site uses Cookies. View our privacy policy here.