Asymmetric synthesis of the core cyclopentane of viridenomycin

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Mark P. Arrington and A. I. Meyers


Abstract

The fully substituted cyclopentene ring with three stereogenic centers has been efficiently constructed for the first time using chiral bicyclic lactams, the insertion of the quaternary center being the key step; ring opening of chiral sulfates to the correct 1,2-dihydroxy substituents also played a major role in reaching 1 in suitable form (18) for further study.


References

  1. M. Nakagawa, K. Furihata, Y. Hayakawa and H. Seto, Tetrahedron Lett., 1991, 32, 659 CrossRef CAS.
  2. T. Hasegawa, T. Kamiya, T. Henmi, H. Iwasaka and S. Yamatodani, J. Antibiot., 1975, 28, 167 CAS.
  3. S. Omura, A. Nakagawa, K. Shibata and H. Sano, Tetrahedron Lett., 1982, 23, 4713 CrossRef CAS; I. Umezawa, H. Takeshima, K. Komiyama, Y. Koh, H. Yamamoto and M. Kawaguchi, J. Antibiot., 1981, 34, 259 CAS.
  4. A. B. Smith, III, T. A. Rano, N. Chida, G. A. Sulikowski and J. L. Wood, J. Am. Chem. Soc., 1992, 114, 8008 CrossRef CAS.
  5. A. I. Meyers and D. Romo, Tetrahedron, 1991, 47, 9503 CrossRef CAS; A. I. Meyers and G. P. Brengel, Chem. Commun., 1997, 1 RSC.
  6. D. A. Sandham and A. I. Meyers, unpublished results.
  7. A. Saito, A. Tanaka and T. Oritani, Tetrahedron: Asymmetry, 1996, 7, 2923 CrossRef CAS.
  8. Y. Gao and K. B. Sharpless, J. Am Chem. Soc., 1988, 110, 7538 CrossRef CAS.
  9. B. Lohray, Synthesis, 1992, 1035 CrossRef CAS.
  10. C. Liotta and T. C. Caruso, Tetrahedron Lett., 1985, 26, 1599 CrossRef CAS.
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