Convergent synthesis of the trans-fused 6-n-6-6 (n = 7–10) tetracyclic ether system based on a ring-closing metathesis reaction

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Tohru Oishi, Yoko Nagumo, Masahiro Hirama, Tohru Oishi, Yoko Nagumo and Masahiro Hirama


Abstract

A convergent synthesis of the trans-fused 6-n-6-6 (n = 7–10) tetracyclic ether system was achieved via stereoselective alkylation and ring-closing metathesis reaction.


References

  1. M. Murata, A. M. Legrand, Y. Ishibashi, M. Fukui and T. Yasumoto, J. Am. Chem. Soc., 1990, 112, 4380 CrossRef CAS; M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada and T. Yasumoto, J. Am. Chem. Soc., 1997, 119, 11 325 CrossRef.
  2. E. Alvarez, M. T. Díaz, L. Hanxing and J. D. Martín, J. Am. Chem. Soc., 1995, 117, 1437 CrossRef CAS; S. Hosokawa and M. Isobe, Synlett, 1995, 1179 CrossRef CAS; M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611 CrossRef CAS.
  3. T. Suzuki, O. Sato, M. Hirama, Y. Yamamoto, M. Murata, T. Yasumoto and N. Harada, Tetrahedron Lett., 1991, 32, 4505 CrossRef CAS; O. Sato and M. Hirama, Synlett, 1992, 705 CrossRef CAS; H. Oguri, S. Hishiyama, T. Oishi and M. Hirama, Synlett, 1995, 1252 CrossRef CAS; T. Oishi, M. Shoji, K. Maeda, N. Kumahara and M. Hirama, Synlett, 1996, 1165 CAS; H. Oguri, S. Hishiyama, O. Sato, T. Oishi, M. Hirama, M. Murata, T. Yasumoto and N. Harada, Tetrahedron, 1997, 53, 3057 CrossRef CAS; T. Oishi, K. Maeda and M. Hirama, Chem. Commun., 1997, 1289 RSC; T. Oishi, M. Shoji, N. Kumahara and M. Hirama, Chem. Lett., 1997, 845 CrossRef CAS.
  4. T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 980 CAS.
  5. W. J. Zuercher, M. Hashimoto and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 6634 CrossRef CAS and references cited therein.
  6. For recent applications of the metathesis reactions to the synthesis of monocyclic and terminal cyclic ether systems, see: K. C. Nicolaou, M. H. D. Postema and C. F. Claiborne, J. Am. Chem. Soc., 1996, 118, 1565 Search PubMed; K. C. Nicolaou, M. H. D. Postema, E. W. Yue and A. Nadin, J. Am. Chem. Soc., 1996, 118, 10335 CrossRef CAS; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 CrossRef CAS; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 127 CrossRef CAS; M. Delgado and J. D. Martín, Tetrahedron Lett., 1997, 38, 6299 CrossRef; M. T. Crimmins and A. L. Choy, J. Org. Chem., 1997, 62, 7548 CrossRef CAS.
  7. D. L. Lewis, J. K. Cha and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 4976 CrossRef CAS.
  8. K. Tomooka, K. Matsuzawa and K. Suzuki, Tetrahedron Lett., 1987, 28, 6339 CrossRef CAS.
  9. H.-J. Liu, J. Yip and K.-S. Shia, Tetrahedron Lett., 1997, 38, 2253 CrossRef CAS.
  10. H. Kotsuki, I. Kadota and M. Ochi, Tetrahedron Lett., 1989, 30, 1281 CrossRef CAS; H. Kotsuki, I. Kadota and M. Ochi, Tetrahedron Lett., 1990, 31, 4609 CrossRef CAS.
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