A concise approach towards the synthesis of steganone analogues

Abstract

The cobalt-mediated [2+2+2] cycloaddition of a tethered deca-1,9-diyne is used as a key step in a highly convergent route to steganone analogues.

References

1. S. M. Kupchan, R. W. Britton, M. F. Ziegler, C. J. Gilmore, R. J. Restivo and R. Bryan, J. Am. Chem. Soc., 1973, 95, 1335.
2. R. W. J. Wang, L. I. Rebbun and M. S. Kupchan, Cancer Res., 1977, 37, 3071.
3. N. S. Narasimhan and I. R. Aiden, Tetrahedron Lett., 1988, 29, 2987; N. S. Narasimhan and I. R. Aiden, Indian J. Chem., Sect. B., 1993, 32B, 211; A. I. Meyers, J. R. Flisak and R. A. Aitken, J. Am. Chem. Soc., 1987, 109, 5446; P. Magnus, J. Schultz and T. Gallagher, J. Am. Chem. Soc., 1985, 107, 4984; R. Dhal, J. P. Robin and E. Brown, Tetrahedron, 1983, 39, 2787; M. Mervic, Y. Ben-David and E. Ghera, Tetrahedron Lett., 1981, 22, 5091; F. E. Ziegler, I. C. Chliwner, K. W. Fowler, S. J. Kanfer, S. J. Kuo and N. D. Sinha, J. Am. Chem. Soc., 1980, 102, 790; E. Brown, R. Dhal and J. P. Robin, Tetrahedron Lett., 1979, 733; E. R. Larson and R. A. Raphael, Tetrahedron Lett., 1979, 5041; G. R. Krow, K. M. Damadoran, E. Michener, R. Wolf and J. Gaure, J. Org. Chem., 1978, 43, 3950; D. Becker, L. R. Hughes and R. A. Raphael, J. Chem. Soc., Perkin Trans. 1, 1977, 1674; L. R. Hughes and R. A. Raphael, Tetrahedron Lett., 1976, 1543; A. S. Kende and L. S. Liebskind, J. Am. Chem. Soc., 1976, 98, 267; M. Uemura, A. Daimon and Y. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1943.
4. D. Becker, L. R. Hughes and R. A. Raphael, J. Chem. Soc., Chem. Commun., 1974, 430.
5. K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 1984, 28, 539.
6. J. F. Tocanne and C. Asselineau, Bull. Chem. Soc. Fr., 1965, 3346.
7. M. E. Garst and B. J. McBride, J. Org. Chem., 1989, 54, 249.
8. F. Ujjainwalla, PhD thesis, University of London, 1993. We are grateful to Drs D. WilliamsA. M. Z. Slawin for the crystal structure determination, which will be discussed in the full paper.
9. R. Gleiter, D. Kratz, M. L. Ziegler and B. Nuber, Tetrahedron Lett., 1990, 31, 6175; C.-A. Chang, J. A. King Jr. and K. P. C. Vollhardt, J. Chem. Soc., Chem. Commun., 1981, 53; C.-A. Chang, C. G. Francisco, T. R. Gadek, J. A. King Jr., E. D. Sternberg and K. P. C. Vollhardt, in Organic Synthesis Today and Tomorrow, ed. B. M. Trost and C. R. Hutchinson, Pergamon, New York, 1981, 71; P. Phanasavath, C. Aubert and M. Malacria, Tetrahedron Lett., 1998, 39, 1561.