Unprecedented and novel hetero [6+3] cycloadditions of fulvene: a facile synthesis of the 11-oxasteroid framework

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Bor-Cherng Hong, Hsu-I Sun and Zhong-Yi Chen


Abstract

In contrast to the Diels–Alder reaction of fulvenes and benzoquinone, 6-dimethylaminofulvene reacts with benzoquinones to give the hetero [6+3] cycloaddition adduct, constituting an efficient and novel route to cyclopenta[c]chromenes including 11-oxasteroids.


References

  1. For a recent review on fulvene chemistry, see: M. Neuenschwander, in The Chemistry of Double-Bonded Functional Groups, ed. S. Patai, Wiley, Chichester, 1989, vol. 2, p. 1131 Search PubMed .
  2. I. Rawson, B. K. Carpenter and H. R. Hoffmann, J. Am. Chem. Soc., 1979, 101, 1786 CrossRef CAS ; R. Noyori, Y. Hayakawa, H. Takaya, S. Murai, R. Kobayashi and N. Sonoda, J. Am. Chem. Soc., 1978, 100, 1759 CrossRef CAS .
  3. K. Imafuku and K. Arai, Synthesis, 1989, 501 CrossRef CAS ; L. A. Paquette, J. A. Colapret and D. R. Andrews, J. Org. Chem., 1985, 50, 201 CrossRef CAS .
  4. M. Harre, P. Raddatz, R. Walenta and E. Winterfeldt, Angew. Chem., Int. Ed. Engl., 1982, 21, 480 CrossRef ; R. Gleiter and O. Borzyk, Angew. Chem., Int. Ed. Engl., 1995, 34, 1001 CAS .
  5. Y. Himeda, H. Yamataka, I. Ueda and M. Hatanaka, J. Org. Chem., 1997, 62, 6529 CrossRef CAS ; V. Nair, A. G. Nair, K. V. Radhakrishnan, M. V. Nadakumar and N. P. Rath, Synlett, 1997, 767 CAS .
  6. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336 CrossRef CAS ; Z.-I. Yoshida, M. Shibata, E. Ogino and T. Sugimoto, Angew. Chem., Int. Ed. Engl., 1985, 24, 60 CrossRef .
  7. M. Suda and K. Hafner, Tetrahedron Lett., 1977, 2453 CrossRef CAS ; T. C. Wu and K. N. Houk, J. Am. Chem. Soc., 1985, 107, 5308 CrossRef CAS .
  8. B.-C. Hong, S.-S. Sun and Y.-C. Tsai, J. Org. Chem., 1997, 62, 7717 CrossRef CAS .
  9. For a recent review in the synthesis of indan systems, see: B.-C. Hong and S. Sarshar, Org. Prep. Proced. Int., 1999, 31, 1 Search PubMed .
  10. For previous papers in this series, see: B.-C. Hong, Z.-Y. Chen and E. S. Kumar, J. Chem. Soc., Perkin Trans. 1, 1999, 1135 Search PubMed ; B.-C. Hong and J.-H. Hong, Tetrahedron Lett., 1997, 38, 255 RSC ; B.-C. Hong and S.-S. Sun, Chem. Commun., 1996, 937 CrossRef CAS .
  11. For the other types of reactions of 6-aminofulvene, see: D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251 Search PubMed ; T. Ishizu, M. Mori and K. Kanematsu, J. Org. Chem., 1981, 46, 526 CrossRef CAS .
  12. A. G. Griesbeck, K. Peters, E.-M. Peters and H. G. Schnering, Angew. Chem., Int. Ed. Engl., 1990, 29, 803 CrossRef ; G. Mehta, S. H. K. Reddy and S. Padma, Tetrahedron, 1991, 47, 7821 CrossRef CAS .
  13. This skeleton is present in many natural products, see: F. A. Davis and B.-C. Chen, J. Org. Chem., 1993, 58, 1751 Search PubMed ; A. Arnoldi, A. Bassoli, G. Borgonovo and L. Merlini, J. Chem. Soc., Perkin Trans. 1, 1995, 2447 CrossRef CAS .
  14. These skeletons occur widely in many natural products, see: K. Shimano, Y. Ge, K. Sakaguchi and S. Isoe, Tetrahedron Lett., 1996, 37, 2253 Search PubMed ; J.-L. Brayer, J.-P. Alazard and C. Thal, Chem. Commun., 1983, 257 CrossRef CAS ; K. C. Joshi, P. Singh, S. Taneja, P. J. Cox, R. A. Howie and R. H. Thomson, Tetrahedron, 1983, 38, 2703 RSC .
  15. R. C. Rastogi, M. N. R. Chowdhury and C. R. Engel, Steroids, 1973, 21, 147 CAS .
  16. H. Suginome, S. Yamada and J. B. Wang, J. Org. Chem., 1990, 55, 2170 CrossRef CAS ; K. Hildebrandt, T. Debaerdemaeker and W. Friedrichsen, Tetrahedron Lett., 1988, 29, 2045 CrossRef CAS .
  17. C. R. Engel, I. H. Ibrahim, D. Mukherjee, R. Szöghy and V. S. Salvi, Heterocycles, 1989, 28, 905 CAS .
  18. S. Takegawa, N. Koizumi, M. Mieda and K. Shibata, Chem. Pharm. Bull., 1996, 44, 746 CAS ; A. Planas, N. Sala and J.-J. Bonet, Helv. Chim. Acta, 1989, 72, 725 CAS ; H. Suginome and J. B. Wang, Bull. Chem. Soc. Jpn., 1989, 62, 193 CAS .
  19. C. R. Engel, S. Salvi and M. N. R. Chowdhury, Steroids, 1975, 25, 781 CrossRef CAS .
  20. For the preparation of 6-dimethylaminofulvene, see: K. Hafner, K. H. Vopel, G. Ploss and C. Konig, Liebigs. Ann. Chem., 1963, 661, 52 Search PubMed .
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