Julia–Colonna asymmetric epoxidation of furyl styryl ketone as a route to intermediates to naturally-occurring styryl lactones

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

Wei-ping Chen and Stanley M. Roberts


Abstract

The enone 1 was oxidized stereoselectively using urea-hydrogen peroxide with polyeucine as the catalyst to give the epoxide 2 which was used to make (+)-goniotriol 7, (+)-goniofufurone 8, (+)-8-acetylgonitriol 9 and gonio-pypyrone 10.


References

  1. B. Lygo and P. G. Wainwright, Tetrahedron Lett., 1998, 39, 1599 CrossRef CAS.
  2. S. Arai, H. Tsuge and T. Shioiri, Tetrahedron Lett., 1998, 39, 7563 CrossRef CAS; K. Daikai, M. Kamaura and J. Inanaga, Tetrahedron Lett., 1998, 39, 7321 CrossRef CAS; S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibasaki, Tetrahedron Lett., 1998, 39, 7353 CrossRef CAS.
  3. For a recent review see J. V. Allen, S. M. Roberts and N. M. Williamson, Adv. Biochem. Eng. Biotechnol., 1998, 63, 125 Search PubMed for earlier reviews see L. Pu, Tetrahedron: Asymmetry, 1998, 9, 1457 Search PubMed; S. Ebrahim and M. Wills, Tetrahedron: Asymmetry, 1997, 8, 3163 Search PubMed.
  4. B. M. Adger, J. V. Barkley, S. Bergeron, M. W. Cappi, B. E. Flowerdew, M. P. Jackson, R. McCague, T. C. Nugent and S. M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1997, 3501 RSC.
  5. Cf. J. V. Allen, S. Bergeron, M. J. Griffths, S. Mukherjee, S. M. Roberts, N. M. Williamson and L. E. Wu, J. Chem. Soc., Perkin Trans. 1, 1998, 3171 Search PubMed.
  6. (a) X. P. Fang, J. E. Anderson, C. J. Chang, J. L. McLaughlin and P. E. Fanwick, J. Nat. Prod., 1991, 54, 1034 CrossRef CAS; (b) X. P. Fang, J. E. Anderson, C. J. Chang and J. L. McLaughlin, Tetrahedron, 1991, 47, 9751 CrossRef CAS; (c) A. Alkofahi, W. W. Ma, T. G. McKenzie, S. R. Byrn and J. L. McLaughlin, J. Nat. Prod, 1989, 52, 1371 CrossRef CAS; (d) A. A. E. El-Zayat, N. R. Ferrighi, T. G. McKenzie, S. R. Byrn, J. M. Cassady, C. J. Chang and J. L. McLaughlin, Tetrahedron Lett., 1985, 26, 955 CrossRef; (e) X. P. Fang, J. E. Anderson, J. F. Kozlowski, C. J. Chang and J. L. McLaughlin, Tetrahedron, 1993, 49, 1563 CrossRef CAS; (f) Y. C. Wu, F. R. Chang, C. Y. Duh, S. K. Wang and T. S. Wu, Phytochemistry, 1992, 31, 2851 CrossRef CAS; (g) Y. C. Wu, C. Y. Duh, F. R. Chang, G. Y. Chang, S. K. Wang, J. J. Chang, D. R. McPhail, A. T. McPhail and K. H. Lee, J. Nat. Prod., 1991, 54, 1077 CrossRef CAS; (h) F. B. Ahmad, S. O. Omar and A. M. Sharif, Phytochemistry, 1991, 30, 2430 CrossRef CAS; (i) S. M. Colegate, L. B. Din, A. Latiff, K. M. Salleh, M. W. Samsudin, B. W. Skelton, K. Tadano, A. H. White and Z. Zakaria, Phytochemistry, 1990, 29, 1701 CrossRef CAS; (j) T. W. Sam, S. Y. Chew, S. Matsjeh, E. K. Gan, D. Razak and A. L. Mohamed, Tetrahedron Lett., 1987, 28, 2541 CrossRef CAS; (k) X. P. Fang, J. E. Anderson, C. J. Chang, P. E. Fanwick and J. L. McLaughlin, J. Chem. Soc., Perkin Trans. 1, 1990, 1655 RSC; (l) A. Bermejo, M. A. Blazquez, A. Serrano, M. C. Zafra-Polo and D. Cortes, J. Nat. Prod., 1997, 60, 1338 CrossRef CAS.
  7. N. Iranpoor, B. Tamami and K. Niknam, Can. J. Chem., 1997, 75, 1913 CAS.
  8. M. P. Georgiadis and E. A. Couladouros, J. Org. Chem., 1986, 51, 2725 CrossRef.
  9. From D- or L-glyceraldehyde acetonide: (a) M. Tsubuki, K. Kanai and T. Honda, J. Chem. Soc., Chem. Commun., 1992, 1640 RSC; (b) M. Tsubuki, K. Kanai and T. Honda, Synlett, 1993, 653 CrossRef CAS; (c) M. Tsubuki, K. Kanai and T. Honda, Heterocycles, 1993, 35, 281 CAS; (d) S. H. Kang and W. J. Kim, Tetrahedron Lett., 1989, 30, 5915 CrossRef CAS.
  10. (a) Z. C. Yang and W. S. Zhou, Tetrahedron, 1995, 51, 1429 CrossRef CAS; (b) Z. C. Yang and W. S. Zhou, J. Chem. Soc., Chem. Commun., 1995, 743 RSC.
  11. From D-glycero-D-glucoheptono-γ-lactone: (a) J. G. Guilhouley and T. K. M. Shing, J. Chem. Soc., Chem. Commun., 1988, 976 RSC; (b) T. K. M. Shing and M. J. Aloui, J. Chem. Soc., Chem. Commun., 1988, 1526 Search PubMed; (c) T. K. M. Shing and M. J. Aloui, Can. J. Chem., 1990, 68, 1035 CAS; (d) T. K. M. Shing, H. C. Tsui and Z. H. Zhou, J. Chem. Soc., Chem. Commun., 1992, 810 RSC; (e) T. K. M. Shing, V. W. F. Tai and H. C. Tsui, J. Chem. Soc., Chem. Commun., 1994, 1293 RSC; (f) T. K. M. Shing, H. C. Tsui and Z. H. Zhou, Tetrahedron Lett., 1993, 34, 691 CrossRef CAS; (g) T. K. M. Shing and H. C. Tsui, J. Chem. Soc., Chem. Commun., 1992, 432 RSC; (h) T. K. M. Shing, H. C. Tsui and Z. H. Zhou, Tetrahedron, 1992, 48, 8659 CrossRef CAS; (i) T. K. M. Shing, Z. H. Zhou and T. C. Mak, J. Chem. Soc., Perkin Trans. 1, 1992, 1907 RSC; (j) T. K. M. Shing, H. C. Tsui and Z. H. Zhou, J. Org. Chem., 1995, 60, 3121 CrossRef CAS.
  12. (a) D. Xu and K. B. Sharpless, Tetrahedron Lett., 1994, 35, 4685 CrossRef CAS; (b) S. Y. Ko and J. Lerpiniere, Tetrahedron Lett., 1995, 36, 2101 CrossRef CAS; (c) W. S. Zhou and Z. C. Yang, Tetrahedron Lett., 1993, 34, 7075 CrossRef CAS; (d) W. S. Zhou and Z. C. Yang, J. Chem. Soc., Perkin Trans. 1, 1994, 3231 RSC; (e) W. S. Zhou and Z. C. Yang, Chin. J. Chem., 1996, 14, 152 Search PubMed; (f) D. J. Dixon, S. V. Ley and E. W. Tate, J. Chem. Soc., Perkin Trans. 1, 1998, 3127 RSC.
  13. From L-arabinose: (a) K. Tadano, Y. Uneno and S. Ogawa, Chem. Lett., 1988, 111 CAS; (b) K. Tadano, Y. Uneno, S. Ogawa and J. L. McLaughlin, Bull. Chem. Soc. Jpn., 1989, 49, 1563.
  14. From D-glucose: (a) T. Gracza and V. Jager, Synlett, 1992, 191 CrossRef CAS; (b) T. Gracza and V. Jager, Synthesis, 1994, 1359 CrossRef CAS; (c) P. J. Murphy, J. Chem. Soc., Chem. Commun., 1992, 1096 RSC; (d) K. P. C. Prakash and S. P. Rao, Synlett, 1993, 123 CrossRef CAS; (e) K. P. C. Prakash and S. P. Rao, Tetrahedron, 1993, 49, 1505 CrossRef CAS; (f) J. P. Gesson, J. C. Jacquesy and M. Mondon, Tetrahedron Lett., 1987, 28, 3945 CrossRef CAS; (g) J. P. Gesson, J. C. Jacquesy and M. Mondon, Tetrahedron Lett., 1987, 28, 3949 CrossRef CAS; (h) J. P. Gesson, J. C. Jacquesy and M. Mondon, Tetrahedron, 1989, 45, 2627 CrossRef CAS.
  15. From L-tartaric acid: (a) P. Somfai, Tetrahedron, 1994, 50, 11315 CrossRef CAS; (b) S. Saito, T. Harunari, N. Shimamura, M. Asahara and T. Morikawa, Synlett, 1992, 325 CrossRef CAS.
  16. From D-glucurono-6,3-lactone: (a) J. Ye, R. K. Bhatt and J. R. Flack, Tetrahedron Lett., 1993, 34, 8007 CrossRef CAS; (b) X. H. Yi, Y. Meng and C. J. Li, Chem. Commun., 1998, 449 RSC; (c) X. H. Yi, Y. Meng, X. G. Hua and C. J. Li, J. Org. Chem., 1998, 63, 7472 CrossRef CAS; (d) J. P. Surivet and J. M. Vatèle, Tetrahedron Lett., 1998, 39, 9681 CrossRef CAS.
  17. From (S)- or (R)-mandelic acid: (a) J. P. Surivet, J. Goré and J. M. Vatèle, Tetrahedron Lett., 1996, 37, 371 CrossRef CAS; (b) J. P. Surivet and J. M. Vatèle, Tetrahedron Lett., 1996, 37, 4373 CrossRef CAS; (c) J. P. Surivet, J. Goré and J. M. Vatèle, Tetrahedron, 1996, 52, 14877 CrossRef CAS; (d) J. P. Surivet, J. N. Volle and J. M. Vatèle, Tetrahedron: Asymmetry, 1996, 7, 3305 CrossRef CAS; (e) J. P. Surivet and J. M. Vatèle, Tetrahedron Lett., 1997, 38, 819 CrossRef CAS; (f) J. P. Surivet and J. M. Vatèle, Tetrahedron Lett., 1998, 39, 7299 CrossRef CAS; (g) M. Kotora and E. Negishi, Tetrahedron Lett., 1996, 37, 9041 CrossRef; (h) J. P. Surivet and J. M. Vatèle, Tetrahedron Lett., 1998, 39, 9681 CrossRef CAS.
  18. By asymmetric aldol reaction: (a) C. Mukai, I. J. Kim and M. Hanaoka, Tetrahedron Lett., 1993, 34, 6081 CrossRef CAS; (b) C. Mukai, S. Hirai, I. J. Kim, M. Kido and M. Hanaoka, Tetrahedron, 1996, 52, 6547 CrossRef CAS; (c) C. Mukai, S. Hirai and M. Hanaoka, J. Org. Chem., 1997, 62, 6619 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.