The Preparation of Furano-steroid Analogues of Demethoxyviridin

Abstract

The syntheses of a C-4:C-6 furano-steroid by the base-catalysed cyclization of 6α-acetoxyandrost-4-ene-3,17-dione and of a C-4:C-6 tetrahydrofuran by the cyclization of 3β,6β-dihydroxy-4β-hydroxymethylandrostan-17-one, are described.

References

1. R. W. Bonser, N. T. Thompson, R. W. Randall, J. E. Tareson, G. D. Spacey, H. F. Hodson and L. G. Garland, Br. J. Pharmacol., 1991, 103, 1237.
2. For a review see, J. R. Hanson, Nat. Prod. Rep., 1995, 12, 381.
3. W. Haefliger, Z. Kis and D. Hauser, Helv. Chim. Acta, 1975, 58, 1620.
4. T. Komeno, S. Ishihara, K. Takigawa, H. Itani and H. Iwakura, Chem. Pharm. Bull., 1969, 17, 2586.
5. M. Ehrenstein and M. T. Decker, J. Org. Chem., 1940, 5, 544.
6. J. R. Hanson, C. Uyanik and K. Yildirim, J. Chem. Res. (S), 1998, 580.
7. R. D. Burnett and D. N. Kirk, J. Chem. Soc., Perkin Trans. 1, 1973, 1830.
8. C. P. Balant and M. Ehrenstein, J. Org. Chem., 1952, 17, 1587.
9. A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
10. H. Nishiyama, T. Kitajima, M. Matsumoto and K. Itoh, J. Org. Chem., 1984, 49, 2298.
11. G. Stork and M. J. Sofia, J. Am. Chem. Soc., 1986, 108, 6826.
12. N. T. Flaih and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1990, 2667.