Diastereospecific approach to (±)-samin and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane (furofuran) lignans using the Ireland–Claisen rearrangement of unsaturated oxamacrolides

Abstract

Enolate Claisen rearrangement of the unsaturated oxamacrolide 28 leads specifically, after reduction, to the tetrahydro-3-furylmethanol 30, via a boat-like transition state 29. Initial attempts to obtain a macrolide related to 28 by O-alkylation of the model β-hydroxy ester 12 using acetimidate 13 were inefficient. Key steps in the successful preparation of the macrolide 28 are Michael addition of a mono-protected (Z)-but-2-ene-1,4-diol 23 to an α-sulfonyl cinnamate 26 and lactonization of the derived hydroxy acid 27c using Mukaiyama’s reagent. Subsequent oxidative cleavage of the vinyl group in the tetrahydrofuran 30 gives (±)-samin 9, a precursor of both symmetrical and unsymmetrical furofuran lignans 8.

References

1. R. E. Ireland, R. H. Mueller and A. K. Willard, J. Am. Chem. Soc., 1976, 98, 2868.
2. S. Danishefsky, R. L. Funk and J. F. Kerwin, J. Am. Chem. Soc., 1980, 102, 6889; S. Danishefsky and K. Tsuzuki, J. Am. Chem. Soc., 1980, 102, 6891.
3. A. G. Cameron and D. W. Knight, J. Chem. Soc., Perkin Trans. 1, 1986, 161; R. L. Funk, T. A. Olmstead, M. Parvez and J. B. Stallmann, J. Org. Chem., 1993, 58, 5873 and references cited therein.
4. R. L. Funk, M. M. Abelman and J. D. Munger, Tetrahedron, 1986, 42, 2831.
5. J. Cooper, D. W. Knight and P. T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 1991, 705; J. Cooper, D. W. Knight and P. T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 1992, 553; R. L. Funk and J. D. Munger, Jr., J. Org. Chem., 1985, 50, 707.
6. For reviews of this area in general, see D. A. Whiting, Nat. Prod. Rep., 1985, 2, 191; 1987, 4, 499; D. C. Ayers and J. D. Loike, Lignans: Chemistry, Biological and Clinical Properties, Cambridge University Press, 1990; R. S. Ward, Tetrahedron, 1990, 46, 5029; R. S. Ward, Nat. Prod. Rep., 1993, 10, 1 For recent work in the area of furofuran synthesis, see K. Mikami, H. Matsueda and T. Nakai, Synlett., 1993, 235; A. van Oeveren, J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 1994, 59, 5999; T. Ogiku, S. Yoshida, H. Ohmizu and T. Iwasaki, J. Org. Chem., 1995, 60, 1148; S. Yoshida, T. Yamanaka, T. Miyake, Y. Moritani, H. Ohmizu and T. Iwasaki, Tetrahedron Lett., 1995, 36, 7271; H. Suginome, K. Orito, K. Yorita, M. Ishikawa, N. Shimoyama and T. Sasaki, J. Org. Chem., 1995, 60, 3052.
7. E. Haslam and R. D. Haworth, J. Chem. Soc., 1955, 827; P. Budowski, J. Am. Oil Chem. Soc., 1964, 41, 280.
8. S. Takano, T. Ohkawa, S. Tamori, S. Satoh and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1988, 189 See also Y. Fukuda, M. Isobe, M. Nagata, T. Osawa and M. Namiki, Heterocycles, 1986, 24, 923.
9. A. Pelter, R. S. Ward, P. Collins, R. Venkateswarlin and I. T. Kay, J. Chem. Soc., Perkin Trans. 1, 1985, 587 and references cited therein.
10. D. R. Stevens and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1990, 425 and references cited therein.
11. G. A. Kraus and L. Chen, J. Am. Chem. Soc., 1990, 112, 3464.
12. S. Takano, K. Samizu and K. Ogasawaara, J. Chem. Soc., Chem. Commun., 1993, 1032; Synlett, 1993, 785.
13. G. Maiti, S. Adhikari and S. C. Roy, Tetrahedron Lett., 1994, 35, 6731; Tetrahedron, 1995, 51, 8389.
14. H. M. Bradley, R. G. Jones and D. W. Knight, Synlett, 1992, 479.
15. For a preliminary communication, see H. M. Bradley and D. W. Knight, J. Chem. Soc., Chem. Commun., 1991, 1641.
16. K. Shimizu and K. Ogasawara, Chem. Lett., 1995, 543.
17. T. Wirth, K. J. Kulicke and G. Fragale, J. Org. Chem., 1996, 61, 2686.
18. U. Widmer, Synthesis, 1987, 568.
19. T. Mukaiyama, M. Usui and K. Saigo, Chem. Lett., 1976, 49.
20. R. L. Funk, M. M. Abelman and K. M. Jellison, Synlett, 1989, 36.
21. R. E. Ireland and D. W. Norbeck, J. Am. Chem. Soc., 1985, 107, 3279.
22. J. D. Elliott, J. Steele and W. S. Johnson, Tetrahedron Lett., 1985, 26, 2535.
23. S. Danishefsky, E. M. Berman, M. Ciufolini, S. J. Etheredge and B. E. Segmuller, J. Am. Chem. Soc., 1985, 107, 3891.
24. C. H. Heathcock and L. A. Flippin, J. Am. Chem. Soc., 1983, 105, 1667.
25. D. Dauzonne and R. Royer, Synthesis, 1987, 399.
26. N. Ono, H. Miyake, R. Tamura and A. Kaji, Tetrahedron Lett., 1981, 22, 1705.
27. N. Ono, H. Miyake and A. Kaji, Chem. Lett., 1985, 635; N. Ono, H. Miyake, A. Kamimura, I. Hamamoto, R. Tamura and A. Kaji, Tetrahedron, 1985, 41, 4013.
28. N. Kornblum, S. C. Carlson and R. G. Smith, J. Am. Chem. Soc., 1979, 101, 647; A. Lytko-Krasuska, H. Piotrowska and T. Urbanski, Tetrahedron Lett., 1979, 1243; N. Ono, R. Tamura and A. Kaji, J. Am. Chem. Soc., 1980, 102, 2851; H. Suzuki, K. Takaoka and A. Osuka, Bull. Chem. Soc. Jpn., 1985, 58, 1067.
29. H. Dressler and J. E. Graham, J. Org. Chem., 1967, 32, 985.
30. B. M. Trost, H. C. Arndt, P. E. Strege and T. R. Verhoeven, Tetrahedron Lett., 1976, 3477.
31. F. Ishibashi and E. Taniguchi, Bull. Chem. Soc. Jpn., 1988, 61, 4361; Chem. Lett., 1989, 313.
32. L. A. Clizbe and L. E. Overman, Org. Synth., 1978, 58, 4.