Bicyclo[3.3.1]nonanes as Synthetic Intermediates. I. Improved Synthetic Methods for Bicyclo[3.3.1]nonan-3-one

Chemical and Pharmaceutical Bulletin

Volumn 26, Issue 1, 1978, Pages 288-295

  Momose, Takefumi ^a   Muraoka, Osamu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

3 methyltricyclo 3.3.1.03,7 nonane; 13C NMR; 1H NMR; bicyclo 3.3.1 nonane systems; cleavage of adamantane; Huang Minlon reduction; Michael aldol condensation; reductive dehalogenation; transannular reaction; purple benzene oxidation

Indexed keywords

EID: 85008044221     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.26.288     Document Type: Article

References (39)

1. A.C. Cope and E.C. Hermann, J. Am. Chem. Soc., 72, 3405 (1950)
2. A.C. Cope, F.S. Fawcett, and G. Munn, J. Am. Chem. Soc., 72, 3399 (1950).
3. C.D. Gutsche, T.D. Smith, M.F. Sloan, J.J.Q. van Ufford, and D.E. Jordan, J. Am. Chem. Soc., 80, 4117 (1958).
4. R. B. Woodward, J. Gosteli, I. Ernest, R.J. Friary, G. Nestler, H. Raman, R. Sitrin, Ch. Suter, and J.K. Whitesell, J. Am. Chem. Soc., 95, 6853 (1973).
5. E.J. Corey, N.M. Weinshenker, T.K. Schaaf, and W. Huber, J. Am. Chem. Soc., 91, 5675 (1969)
6. E.J. Corey, U. Koelliker, and J. Neuffer, J. Am. Chem. Soc., 93, 1489 (1971)
7. E.J. Corey, H. Shirahama, H. Yamamoto, S. Terashima, A. Venkateswarlu, and T.K. Schaaf, J. Am. Chem. Soc., 93, 1490 (1971)
8. E.J. Corey, S.M. Albonico, U. Koelliker, T.K. Schaaf, and R.K. Varma, J. Am. Chem. Soc., 93, 1491 (1971)
9. E.J. Corey and G. Moinet, J. Am. Chem. Soc., 95, 6831 (1973)
10. T. Masamune, S. Numata, H. Matsue, and A. Matsuyuki, Bull. Chem. Soc. Jpn., 48, 2294 (1975)
11. T. Masamune and H. Matsue, Chem. Lett., 1975, 895
12. A. Murai, H. Murase, H. Matsue, and T. Masamune, Tetrahedron Lett., 1977, 2507.
13. B.L. Buchanan, “Topics in Carbocyclic Chemistry,” Vol. I, ed. by D. Lloyd, Logos Press Ltd., London, 1969, pp. 199—247
14. Yuki Gosei Kagaku Kyokai Shi, 28, 682 (1970)
15. R. Keese, [Angew. Chem. Int. Ed. Engl., 14, 528 (1975)
16. C.A. Grob, Angew. Chem. Int. Ed. Engl., 15, 569 (1976)
17. J.P. Schaefer, J.C. Lark, C.A. Flegal, and L.M. Honig, J. Org. Chem., 32, 1372 (1967)
18. H.K. Hall, Jr., J. Org. Chem., 28, 3213 (1963)
19. W.G. Dauben and C.D. Poulter, J. Org. Chem., 33, 1237 (1968).
20. L. N. Owen and P.N. Smith, J. Chem. Soc., 1952, 4035
21. C.H. DePuy and K.L. Eilers, “Organic Syntheses,” Coll. Vol. V, ed. by H.E. Baumgarten, John Wiley and Sons, Inc., New York, 1973, p. 326.
22. J.E. Baldwin, J.C.S. Chem. Commun., 1976, 734.
23. J.E. Baldwin and L.I. Kruse, J.C.S. Chem. Commun., 1977, 233.
24. E.W. Garbisch, Jr., J. Org. Chem., 30, 2109 (1965).
25. R.C. Fort, Jr. and P.V.R. Schleyer, Chem. Rev., 64, 277 (1964)
26. R.C. Bingham and P.V.R. Schleyer, “Topics in Current Chemistry,” Vol. 18, Springer Verlag, Berlin, 1971, pp. 32—40
27. E. Osawa, P.V.R. Schleyer, R.C. Bingham, and E.M. Engler, Kagaku No Ryoiki, 27, 365 (1973)
28. M. Nakazaki and K. Naemura, Yuki Gosei Kagaku Kyokai Shi, 32, 905 (1974).
29. G.L. Baughman, J. Org. Chem., 29, 238 (1964)
30. E.R. Talaty, A.E. Cancienne, Jr., and A.E. Dupuy, Jr., J. Chem. Soc., (C), 1968, 1902.
31. H. Stetter and P. Tacke, Chem. Ber., 96, 694 (1963).
32. M. Eakin, J. Martin, and W. Parker, Chem. Commun., 1965, 206.
33. Jih-Hua Liu, G.A. Gauger, and P. Kovacic, J. Org. Chem., 38, 543 (1973)
34. Jih-Hua Liu and P. Kovacic, J. Org. Chem., 38, 3462 (1973).
35. R.A. Appleton and S.H. Graham, Chem. Commun., 1965, 297.
36. D.J. Sam and H.E. Simmons, J. Am. Chem. Soc., 94, 4024 (1972).
37. K. Kimoto and M. Kawanisi, Chem. and Ind., 1971, 1174
38. T. Mori, K.H. Yang, K. Kimoto, and H. Nozaki, Tetrahedron Lett., 1970, 2419.
39. T. Norin and L. Westfelt, Acta Chem. Scand., 17, 1828 (1963).