A silicon controlled total synthesis of the antifungal agent (+)-preussin

Abstract

A stereoselective total synthesis of (+)-preussin has been achieved from a meso anhydride featuring a dimethyl(phenyl)silyl group as a masked hydroxy group which also restricts elimination reactions, stereodirects hydrogenation and ester enolate alkylation, and facilitates Curtius reaction.

References

1. R. E. Schwartz, J. Liesch, O. Hensens, L. Zitano, S. Honeycutt, G. Garrity, R. A. Fromtling, J. Onishi and R. Monaghan, J. Antibiot., 1988, 41, 1774; R. E. Schwartz, J. C. Onishi, R. L. Monaghan, J. M. Liesch and O. D. Hensens, US P 4 847 284, 1989; J. H. Johnson, D. W. Phillipson and A. D. Kahle, J. Antibiot., 1989, 42, 1184.
2. C. S. Pak and G. H. Lee, J. Org. Chem., 1991, 56, 1128.
3. (a) P. L. McGrane and T. Livinghouse, J. Am. Chem. Soc., 1993, 115, 11 485; (b) M. Overhand and S. M. Hecht, J. Org. Chem., 1994, 59, 4721; (c) W. Deng and L. E. Overman, J. Am. Chem. Soc., 1994, 116, 11 241.
4. M. Shimazaki, F. Okazaki, F. Nakajima, T. Ishikawa and A. Ohta, Heterocycles, 1993, 36, 1823.
5. (a) P. D. Theisen and C. H. Heathcock, J. Org. Chem., 1993, 58, 142 and references cited; (b) D. S. Karanewsky, M. F. Malley and J. Z. Gougoutas, J. Org. Chem., 1991, 56, 3744.
6. I. Fleming, R. Henning, D. C. Parker, H. E. Plaut and P. E. J. Sanderson, J. Chem. Soc., Perkin Trans. 1, 1995, 317.
7. R. A. N. C. Crump, I. Fleming, J. H. M. Hill, D. Parker, N. L. Reddy and D. Waterson, J. Chem. Soc., Perkin Trans. 1, 1992, 3277.
8. P. F. Hudrlik, A. M. Hudrlik, T. Yimenu, M. A. Waugh and G. Nagendrappa, Tetrahedron, 1988, 44, 3791.
9. K. Takeshita, Y. Seki, K. Kawamoto, S. Murai and N. Sonoda, J. Org. Chem., 1987, 52, 4864.
10. I. Fleming, Stereocontrol in Organic Synthesis Using Silicon Compounds, Conferencias Plenarias de la XXIII Reunio'n Bienal de Qui'mica, Salamanca, 1990, p. 89.
11. I. Fleming and S. K. Ghosh, J. Chem. Soc., Chem. Commun., 1994, 2285.
12. D. A. Evans, T. C. Britton, R. L. Dorow and J. F. Dellaria, Jr., Tetrahedron, 1988, 44, 5525.
13. T. H. Chan, M. A. Brook and T. Chaly, Synthesis, 1983, 203.
14. H. E. Baumgarten, H. L. Smith and A. Staklis, J. Org. Chem., 1975, 40, 3554.