Enantioselective synthesis of benzylbutyrolactones from 5-hydroxyfuran-2(5H )-one. New chiral synthons for dibenzylbutyrolactone lignans by a chemoenzymatic route

Abstract

A chemoenzymatic method is described for the asymmetric synthesis of benzylbutyrolactones. (R )-5-Acetoxyfuran-2(5H )-one (12) was obtained with ee > 99% in a multigram scale catalytic esterification using immobilized lipase PS. The addition of lithiated dithianes to chiral synthon 12 was followed by an effective multistep reduction to produce enantiomerically pure benzylbutyrolactones.

References

1. D. Ayres and J. D. Loike, Lignans, Cambridge University Press, 1990.
2. A. van Oeveren, J. F. G. A. Jansen and B. L. Feringa, J. Org. Chem., 1994, 59, 5999.
3. R. D. Haworth, Annu. Rep. Prog. Chem., 1936, 33, 266.
4. J. Gnabre, R. Chih, C. Huang, R. B. Bates, J. J. Burns, S. Caldera, M. E. Malcomson and K. J. McClure, Tetrahedron, 1995, 51, 12203.
5. T. Itoh, J. Chika, Y. Takagi and S. Nishiyama, J. Org. Chem., 1993, 58, 5717.
6. K. Tsuji, Y. Terao and K. Achiwa, Tetrahedron Lett., 1989, 30, 6189.
7. J. W. Bode, M. P. Doyle, M. N. Protopopova and Q. L. Zhou, J. Org. Chem., 1996, 61, 9146.
8. J. P. Robin and Y. Landais, Tetrahedron, 1992, 48, 819.
9. A. Pelter, R. S. Ward, D. Martin Jones and P. Maddocks, Tetrahedron: Asymmetry, 1990, 1, 857.
10. A. Pelter, R. S. Ward, D. Martin Jones and P. Maddocks, J. Chem. Soc., Perkin Trans. 1, 1993, 2621; 1993;, 2631.
11. R. S. Ward, Synthesis, 1992, 719.
12. J. F. G. A. Jansen, PhD Thesis, University of Groningen, 1991.
13. H. van der Deen, A. D. Cuiper, R. P. Hof, A. van Oeveren, B. L. Feringa and R. M. Kellogg, J. Am. Chem. Soc., 1996, 118, 3801.
14. H. van der Deen, R. P. Hof, A. van Oeveren, B. L. Feringa and R. M. Kellogg, Tetrahedron Lett., 1994, 45, 8441.
15. B. L. Feringa, Recl. Trav. Chim., 1987, 106, 481.
16. I. Maeba, M. Suzuki, O. Hara, T. Takeuchi, T. Iijima and H. Furukawa, J. Org. Chem., 1987, 52, 4521.
17. R. M. Moriarty, R. K. Vaid, T. E. Hopkins, B. K. Vaid and A. Tuncay, Tetrahedron Lett., 1989, 30, 3019.
18. F. Yuste and R. Sánchez-Obregón, J. Org. Chem., 1982, 47, 3665.
19. B. S. Ong, Tetrahedron Lett., 1980, 21, 4225.
20. J. F. G. A. Jansen and B. L. Feringa, Synth. Commun., 1992, 22, 1367.
21. R. Bovara, G. Carrea, L. Ferrara and S. Riva, Tetrahedron: Asymmetry, 1991, 2, 931.
22. N. Rehnberg and G. Magnusson, J. Org. Chem., 1990, 55, 4340.
23. Not all signals were resolved due to overlap.
24. M. Kuhn and A. von Wartburg, Helv. Chim. Acta, 1967, 50, 1546.
25. E. Brown and A. Daugan, Tetrahedron Lett., 1986, 27, 32, 3719.