Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of a (±)-carbacyclin analogue with the geometry of the exocyclic double bond controlled by the protodesilylation of an allylsilane

Abstract

The known ketone, 7-tert-butyldimethylsilyloxybicyclo[3.3.0]oct-8-en-2-one 11, was converted in five steps into 3-(4′-methoxycarbonylbutylidene)-7-tert-butyldimethylsilyloxy-8-cyanobicyclo[3.3.0]octan-2-one 13. Reduction gave the diastereoisomeric pair of allylic alcohols 14 and 15, both of which were converted into the allylsilane, 3-(1′-dimethylphenylsilyl-4′-methoxycarbonyl)butyl-7-tert-butyldimethylsilyloxy-8-cyanobicyclo[3.3.0]oct-2-ene 20. Protodesilylation of the allylsilane gave a high level of selectivity (>96∶4) in favour of the carbacyclin analogue, 5-(4′-methoxycarbonyl)butylidene-3-tert-butyldimethylsilyloxy-2-cyanobicyclo[3.3.0]octane 22, having the exocyclic double bond with the E-configuration.

References

1. T. Hayashi, M. Konishi, H. Ito and M. Kumuda, J. Am. Chem. Soc., 1982, 104, 4962; T. Hayashi, M. Konishi and M. Kumada, J. Am. Chem. Soc., 1982, 104, 4963; T. Hayashi, H. Ito and M. Kumada, Tetrahedron Lett., 1982, 23, 4605; T. Hayashi, M. Konishi and M. Kumada, J. Chem. Soc., Chem. Commun., 1983, 736; T. Hayashi, K. Kabeta, T. Yamamoto, K. Tamao and M. Kumuda, Tetrahedron Lett., 1983, 24, 5661; T. Hayashi, Y. Okamoto, K. Kabeta, T. Hagihara and M. Kumada, J. Org. Chem., 1984, 49, 4224; T. Hayashi, M. Konishi, Y. Okamoto, K. Kabeta and M. Kumada, J. Org. Chem., 1986, 51, 3772; T. Hayashi, Y. Matsumoto and Y. Ito, Organometallics, 1987, 6, 884; H. Wetter and P. Scherer, Helv. Chim. Acta, 1983, 66, 118; V. G. Matassa, P. R. Jenkins, A. Kümin, L. Damm, J. Schreiber, D. Felix, E. Zass and A. Eschenmoser, Isr. J. Chem., 1989, 29, 321; G. Wickham and W. Kitching, Organometallics, 1983, 2, 541; G. Wickham, D. Young and W. Kitching, Organometallics, 1988, 7, 1187; W. Kitching, K. G. Penman, B. Laycock and I. Maynard, Tetrahedron, 1988, 44, 3819.
2. M. J. C. Buckle and I. Fleming, Tetrahedron Lett., 1993, 34, 2383.
3. I. Fleming and N. K. Terrett, J. Organomet. Chem., 1984, 264, 99.
4. E. Vedejs and C. K. McClure, J. Am. Chem. Soc., 1986, 108, 1094.
5. I. Fleming and D. Higgins, J. Chem. Soc., Perkin Trans. 1, 1992, 3327.
6. I. Fleming, N. J. Lawrence, A. K. Sarkar and A. P. Thomas, J. Chem. Soc., Perkin Trans. 1, 1992, 3303.
7. D. P. Curran and B. H. Kim, Synthesis, 1986, 312.
8. H. Felkin, C. Frajerman and G. Roussi, Ann. Chim. (Paris), 1971, 6, 17; M. El Idrissi and M. Santelli, J. Org. Chem., 1988, 53, 1010.
9. R. C. Nickolson, M. H. Town and H. Vorbrüggen, Med. Chem. Rev., 1985, 5, 1.
10. B. J. R. Whittle and S. Moncada, Prog. Med. Chem., 1984, 21, 237.
11. M. Mori, reported in M. Shibasaki, J. Ueda and S. Ikegami, Tetrahedron Lett., 1979, 433; D. R. Morton Jr. and F. C. Brokaw, J. Org. Chem., 1981, 46, 4808.
12. H. Rehwinkel, J. Skupsch and H. Vorbrüggen, Tetrahedron Lett., 1988, 29, 1775; H.-J. Gais, G. Schmiedle, W. A. Ball, J. Bund, G. Hellman and I. Erdelmeier, Tetrahedron Lett., 1988, 29, 1773; D. K. Hutchinson and P. L. Fuchs, J. Am. Chem. Soc., 1987, 109, 4755; M. Shibasaki, M. Sodeoka and Y. Ogawa, J. Org. Chem., 1984, 49, 4096; M. Sodeoka, S. Satoh and M. Shibasaki, J. Am. Chem. Soc., 1988, 110, 4823; I. Edelmeier and H.-J. Gais, J. Am. Chem. Soc., 1989, 111, 1125.
13. K. C. Nicolaou, W. J. Sipio, R. L. Magolda, S. Seitz and W. E. Barnette, J. Chem. Soc., Chem. Commun., 1978, 1067; K. Kojima and K. Sakai, Tetrahedron Lett., 1978, 29, 3743; C. Gandolfi, Symposium on the Chemistry & Biochemistry of Prostanoids, Salford, July 1978; W. Skuballa, E. Schillinger, C.-St. Stürzebecher and H. Vorbrüggen, J. Med. Chem., 1986, 29, 313.
14. I. Fleming and D. Higgins, Tetrahedron Lett., 1989, 30, 5777; I. Fleming, D. Higgins and A. K. Sakar, in Selectivities in Lewis Acid Promoted Reactions, ed. D. Schinzer, Kluwer, Dordrecht, 1989, pp. 265–280.
15. M. F. Haslanger and S. Ahmed, J. Org. Chem., 1981, 46, 4808.
16. W. Nagata, S. Hirai, H. Itazaki and K. Takeda, J. Org. Chem., 1961, 26, 2413.
17. T. Utimoto, Y. Wakabayashi, T. Horiie, M. Inoue, Y. Shishiyama, M. Obayashi and H. Nozaki, Tetrahedron, 1983, 39, 967.
18. M. F. Haslanger, US P 4,192,891, 1980; Chem. Abstr., 1981, 94, 15282h.
19. I. Paterson, Tetrahedron, 1988, 44, 4207.
20. A. L. Gemal and J.-L. Luche, J. Am. Chem. Soc., 1981, 103, 5454.
21. J. A. Dodge, J. I. Trujillo and M. Presnell, J. Org. Chem., 1994, 59, 234; P. J. Harvey, M. von Itzstein and I. D. Jenkins, Tetrahedron, 1997, 53, 3933.
22. I. Fleming, D. Higgins, N. J. Lawrence and A. P. Thomas, J. Chem. Soc., Perkin Trans. 1, 1992, 3331.
23. M. Suzuki, H. Koyano and R. Noyori, J. Org. Chem., 1987, 52, 5583; M. Shibasaki, H. Fukasawa and S. Ikegami, Tetrahedron Lett., 1983, 24, 3497; A. Takahashi and M. Shibasaki, Tetrahedron Lett., 1987, 28, 1893.
24. K. V. Schenker, W. von Philipsborn, C. A. Evans, W. Skuballa and G.-A. Hoyer, Helv. Chim. Acta, 1986, 69, 1718.
25. J. K. Crandall, D. B. Banks, R. A. Colyer, R. J. Watkins and J. P. Arrington, J. Org. Chem., 1968, 33, 423.
26. M. Huckstep and R. J. K. Taylor, Synthesis, 1982, 881.