An intramolecular rhodium carbenoid C–H insertion approach to chiral isotwistanes. Synthesis of (–)-neopupukean-4,10-dione and (–)-neopupukean-10-one

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A. Srikrishna and Santosh J. Gharpure


Abstract

The first synthesis of a chiral neopupukeanane starting, from (R)-carvone and employing a double Michael reaction and a regioselective intramolecular rhodium carbenoid C–H insertion reaction as key steps, is described.


References

  1. P. Karuso, A. Poiner and P. J. Scheuer, J. Org. Chem., 1989, 54, 2095 CrossRef CAS.
  2. A. T. Pham, T. Ichiba, W. Y. Yoshida, P. J. Scheuer, T. Uchida, J.-i. Tanaka and T. Higa, Tetrahedron Lett., 1991, 32, 4843 CrossRef CAS.
  3. A. Srikrishna, P. Hemamalini and G. V. R. Sharma, J. Org. Chem., 1993, 58, 2509 CrossRef CAS; A. Srikrishna and T. J. Reddy, J. Chem. Soc., Perkin Trans. 1, 1997, 3293 RSC.
  4. To the best of our knowledge, there are no reports in the literature of the synthesis of either racemic or chiral neopupukeanane carbon frameworks.
  5. T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091 CrossRef CAS; M. P. Doyle, in Comprehensive Organometallic Chemistry II, ed. L. S. Hegedus, Pergamon Press, New York, 1995, vol. 12, ch. 5.2 Search PubMed; M. P. Doyle, Aldrichim. Acta, 1996, 29, 3 Search PubMed.
  6. R.-B. Zhao, Y.-F. Zhao, G. Q. Song and Y.-L. Wu, Tetrahedron Lett., 1990, 31, 3559 CrossRef CAS.
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