Stereocontrol in organic synthesis using silicon-containing compounds. A formal synthesis of (±)-thienamycin

Abstract

The lithium enolate Z-11 derived from methyl 3-dimethyl(phenyl)silylbutanoate reacts with the N-silylimines of cinnamaldehyde 12, of 3-trimethylsilylpropynal 18, and of 3-trimethylsilylpropenal 19 to give β-lactams with a high level of stereoselection in favour of the cis isomers 13, 20 and 21, respectively. The dimethyl(phenyl)silyl group in the N-benzyldihydro derivative of the β-lactam 13 was converted into a hydroxy group by protodesilylation followed by peracid oxidation. The aldol product 24 of acetaldehyde with the same enolate Z-11 was converted into the corresponding O-benzyl hydroxamate 25, which gave the trans-β-lactam 26 by a Mitsunobu reaction. A similar aldol reaction using 3-dimethyl(phenyl)silylpropanal and the lithium Z-enolate derived from benzyl 3-dimethyl(phenyl)silylbutanoate gave the aldol 32, which was converted successively by way of the O-benzyl hydroxamate 33 and the trans-β-lactam 34 into the disilylated trans-β-lactam 35. Silyl-to-hydroxy conversion of both silyl groups and N,O-acetonide formation gave the known intermediate 36. Another Mitsunobu reaction with formic acid gave the C-8 epimer 2, which has previously been converted into (±)-thienamycin 1.

References

1. G. Albers-Schonberg, B. H. Arison, O. D. Hensens, J. Hirshfield, K. Hoogsteen, E. A. Kaczka, R. E. Rhodes, J. S. Kahan, F. M. Kahan, R. W. Ratcliffe, E. Walton, L. J. Ruswinkle, R. B. Morin and B. G. Christensen, J. Am. Chem. Soc., 1978, 100, 6491.
2. Reviews: T. Kametani, Heterocycles, 1982, 17, 463; M. Shibuya, J. Synth. Org. Chem., Jpn., 1983, 41, 62; R. Labia and C. Moris, J. Antibiot., 1984, 37, 103; G. I. Georg, in Studies in Natural Product Chemistry, ed. A.-ur Rahman, Elsevier, Amsterdam, 1989, vol. 4, p. 431More recent syntheses: S. Hanessian, D. Desilet and Y. Bennani, J. Org. Chem., 1990, 55, 3098; J. Montgomery, G. M. Wieber and L. Hegedus, J. Am. Chem. Soc., 1990, 112, 6255; N. Ikota, O. Yoshino and K. Koga, Chem. Pharm. Bull., 1991, 39, 2201; J. H. Bateson, S. C. M. Fell, R. Southgate, D. S. Eggleston and P. W. Baures, J. Chem. Soc., Perkin Trans. 1, 1992, 1305; Y. Yamamoto, N. Asao and T. Uyehara, J. Am. Chem. Soc., 1992, 114, 5427; Y. Kitagi, N. Shibata, T. Miki, Y. Takemura and O. Tamura, Chem. Pharm. Bull., 1992, 40, 12; G. Pattenden and S. J. Reynolds, J. Chem. Soc., Perkin Trans. 1, 1994, 379; H. Ishibashi, C. Kameoka, H. Iriyama, K. Kodama, T. Sato and M. Ikeda, J. Org. Chem., 1995, 60, 1276; P. A. Jacobi, S. Murphee, F. Ruprecht and W. Zheng, J. Org. Chem., 1996, 61, 2413; S. G. Davies, C. J. R. Hedgecock and J. M. McKenna, Tetrahedron: Asymmetry, 1996, 6, 2507; L. Banfi, G. Guanti and M. T. Zannetti, Tetrahedron Lett., 1996, 37, 521; S. G. Davies and D. R. Fenwick, Chem. Commun., 1997, 565.
3. F. A. Bouffard, D. B. R. Johnston and B. G. Christensen, J. Org. Chem., 1980, 45, 1130; S. M. Schmitt, D. B. R. Johnston and B. G. Christensen, J. Org. Chem., 1980, 45, 1135; S. M. Schmitt, D. B. R. Johnston and B. G. Christensen, J. Org. Chem., 1980, 45, 1142.
4. I. Fleming and J. D. Kilburn, J. Chem. Soc., Perkin Trans. 1, 1992, 3295.
5. I. Fleming, Chemtracts: Org. Chem., 1996, 9, 1; G. R. Jones and Y. Landais, Tetrahedron, 1996, 37, 7599; K. Tamao, Adv. Silicon Chem., JAI Press, Greenwich, CT, 1996, 3, 1.
6. I. Fleming and J. D. Kilburn, J. Chem. Soc., Chem. Commun., 1986, 1198.
7. S. Danishefsky, A. Guingant and M. Prisbylla, Tetrahedron Lett., 1980, 21, 2033.
8. I. Fleming, R. Henning, D. C. Parker, H. E. Plaut and P. E. J. Sanderson, J. Chem. Soc., Perkin Trans. 1, 1995, 317.
9. D. J. Hart and D. C. Ha, Chem. Rev., 1989, 89, 1447.
10. C. Palomo, J. M. Aizpurua, R. Urchegui and M. Iturburu, J. Org. Chem., 1992, 57, 1571.
11. D.-C. Ha, D. J. Hart and T.-K. Yang, J. Am. Chem. Soc., 1984, 106, 4819.
12. G. Zweifel and S. J. Backlund, J. Am. Chem. Soc., 1977, 99, 3184; G. Zweifel and H. Arzoumanian, J. Am. Chem. Soc., 1967, 89, 291.
13. G. Stork and E. Colvin, J. Am. Chem. Soc., 1971, 93, 2080.
14. P. F. Hudrlik, A. M. Hudrlik and A. K. Kulkarni, J. Am. Chem. Soc., 1985, 107, 4260.
15. P. F. Hudrlik, J. P. Arcoleo, R. H. Schwartz, R. N. Misra and R. J. Rona, Tetrahedron Lett., 1977, 591.
16. I. Fleming and N. K. Terrett, J. Organomet. Chem., 1984, 264, 99; W. Bernhard and I. Fleming, J. Organomet. Chem., 1984, 271, 281.
17. A. G. Brown, D. F. Corbett, A. J. Eglington and T. T. Howarth, J. Chem. Soc., Chem. Commun., 1977, 523; D. F. Corbett, A. J. Eglington and T. T. Howarth, J. Chem. Soc., Chem. Commun., 1977, 953; A. G. Brown, D. F. Corbett, A. J. Eglington and T. T. Howarth, J. Antibiotics, 1979, 32, 961.
18. W. F. Huffman, K. G. Holden, T. F. Buckley, III, J. G. Gleason and L. Wu, J. Am. Chem. Soc., 1977, 99, 2352; R. Zamboni and G. Just, Can. J. Chem., 1979, 57, 1945; D. R. Kronenthal, C. Y. Han and M. K. Taylor, J. Org. Chem., 1982, 47, 2765; B. Ernest and D. Bellus, German Patent, DE 3 620 467, 1987(Chem. Abstr., 1987, 106, 176 045); C. Palomo, F. P. Cossio, J. M. Odriozola, M. Oiarbide and J. M. Ontoria, Tetrahedron Lett., 1989, 30, 4577; C. Palomo, J. M. Ontoria, J. M. Odriozola, J. M. Aizpurua and I. Ganboa, J. Chem. Soc., Chem. Commun., 1990, 248.
19. P. G. Mattingly and M. J. Miller, J. Org. Chem., 1980, 45, 410; M. J. Miller, P. G. Mattingly, M. A. Morrison and J. F. Kerwin, Jr., J. Am. Chem. Soc., 1980, 102, 7026.
20. K. Baum, D. A. Lerdal and J. S. Horn, J. Org. Chem., 1978, 43, 203.
21. E. J. Corey and G. Schmidt, Tetrahedron Lett., 1979, 399.
22. D. F. Corbett, S. Coulton and R. Southgate, J. Chem. Soc., Perkin Trans. 1, 1982, 3011.
23. J. Graymore, J. Chem. Soc., 1931, 1490.
24. H. Kritzler, K. Wagner and H. Holtschmidt, Belg P 621 378 (Chem. Abstr., 1963, 59, 9816f).
25. S. E. Denmark and T. K. Jones, J. Org. Chem., 1982, 47, 4595.
26. M. J. Carter, I. Fleming and A. Percival, J. Chem. Soc., Perkin Trans. 1, 1981, 2415.
27. K. Baum, D. A. Lerdal and J. S. Horn, J. Org. Chem., 1978, 43, 203.
28. R. A. Benkeser and D. J. Foster, J. Am. Chem. Soc., 1952, 74, 5314.
29. J. W. Wilt, W. K. Chwang, C. F. Dockus and N. M. Tomiuk, J. Am. Chem. Soc., 1978, 100, 5534.
30. I. Fleming, S. Gil, A. K. Sarkar and T. Schmidlin, J. Chem. Soc., Perkin Trans. 1, 1992, 3351.