Transannular cyclization with grignard reagents: Facile synthetic routes to oxaadamantane and protoadamantane derivatives

Synlett

Volumn , Issue 3, 2008, Pages 405-409

  Mlinarić Majerski, Kata ^a   Kragol, Goran ^a,b   Ramljak, Tatjana Šumanovac ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Adamantane derivatives; Grignard reactions; Protoadamantane derivatives; Rearrangements; Transannular cyclization

Indexed keywords

ADAMANTANE DERIVATIVE; GRIGNARD REAGENT;

ARTICLE; CYCLIZATION;

EID: 39749116194     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032054     Document Type: Article

References (41)

1. Cage Hydrocarbons; Olah, G. A., Ed.; Wiley: New York, 1990.
2. Yurchenko, A. In Cage Hydrocarbons; Olah, G. A., Ed.; Wiley: New York, 1990, Chap. 5.
3. (a) Zefirov, N. S.; Averina, N. V. Zh. Org. Khim. 1969, 5, 190.
4. (b) Averina, N. V.; Zafirev, N. S. Zh. Org. Khim. 1969, 5, 1991.
5. (c) Zefirov, N. S.; Tartakovski, V. A.; Averina, N. V. Zh. Org. Khim. 1971, 7, 504.
6. (a) Stetter, H.; Mayer, J. Chem. Ber. 1959, 92, 2664.
7. (b) Schaefer, J. P.; Honig, L. M. J. Org. Chem. 1968, 33, 2655.
8. (a) Black, R. M.; Gill, G. B.; Hands, D. J. Chem. Soc., Chem. Commun. 1972, 311.
9. (b) Krasutsky, P. A.; Kolomitsin, I. V.; Carlson, R. M.; Jones, M. J. r. Tetrahedron Lett. 1996, 37, 5673.
10. Grignard Reagents: New Developments; Richey, H. G. Jr., Ed.; Wiley: Chichester, 2000.
11. (a) Gagneux, A. R.; Meier, R. Tetrahedron Lett. 1969, 1365.
12. (b) Mori, T.; Yang, K. H.; Kimoto, K.; Nozaki, H. Tetrahedron Lett. 1970, 2419.
13. (c) Stepanov, F. N.; Utochka, T. N.; Yurchenko, A. G. Z. Org. Khim. 1972, 8, 1183.
14. 4. The solvent was evaporated under reduced pressure and crude product was purified on silica gel column. (b) Method B: A solution of 7-exo-epoxymethylenbicyclo[3.3.1]nonan-3-one (7) in anhyd THF was added to a solution of Grignard reagent preheated to 55°C. The reaction mixture was heated for 1 h at 55°C, and after workup the products were separated by column chromatography.
15. 2: C, 74.19; H, 9.34. Found: C, 74.19; H, 9.21.
16. 2: C, 72.49; H, 9.95. Found: C, 72.57; H, 9.86. Method B A solution of epoxy ketone 7 (0.50 g, 3.00 mmol)was added to a solution of MeMgI (10.40 mmol) preheated to 35°C. After column chromatography there was obtained 0.035 g (7%) of oxaadamantane 2, 0.23 g (45%) of exo-diol 6, and 0.14 g (27%) of endo-diol 5.
17. 4. After column chromatography 0.02 g (10%) of oxaadamantane 2, 0.09 g (44%) of exo-diol 6, and 0.05 g (25%) of endo-diol 5 were obtained.
18. The calculations were performed by AM1 and PM3 methods implemented in HyperChem 5.0, Hypercube, Gainsville, Florida, USA. The enthalpy of formation for endo-derivatives were found to be higher approximately 1.27 (AM1) or 1.15 (PM3) kcal/mol for 3 and 0.37 (AM1) or 0.88 (PM3) kcal/mol for derivative 5, respectively.
19. Kolocouris, N.; Zoidis, G.; Fytas, C. Synlett 2007, 1063.
20. Majerski, Z.; Hameršak, Z. Org. Synth., Coll. Vol. VI 1988, 958.
21. +]: 178.135216; found: 178.129036.
22. (a) Lenoir, D.; Raber, D. J.; von R. Schleyer, P. J. Am. Chem. Soc. 1974, 96, 2149.
23. (b) Lenoir, D.; von R. Schleyer, P. J. Chem. Soc., Chem. Commun. 1970, 941.
24. Muraoka, O.; Wang, Y.; Okumura, M.; Nishiura, S.; Tanabe, G.; Momose, T. Synth. Commun. 1996, 26, 1555.
25. Yurchenko, A. G.; Melnik, N. N.; Likhotvorik, I. R. Tetrahedron Lett. 1989, 30, 3653.
26. (a) Liu, J.-H.; Kovacic, P. J. Org. Chem. 1973, 38, 3462.
27. (b) Wiesmann, R. F.; Rademacher, P. Chem. Ber. 1994, 127, 1517.
28. 2 as eluent to afford 0.065 g (28%) of exo-diol 4 and 0.08 g (32%) of endo- diol 3.
29. (a) Herpers, E.; Kirmse, W. J. Chem. Soc., Chem. Commun. 1993, 160.
30. (b) Gappa, A.; Herpers, E.; Herrmann, R.; Hülsewede, V.; Kappert, W.; Klar, M.; Kirmse, W. J. Am. Chem. Soc. 1995, 117, 12096.
31. 2: C, 72.49; H, 9.95. Found: C, 72.42; H, 9.72.
32. (a) von R. Schleyer, P.; Lenoir, D.; Mison, P.; Liang, G.; Surya Prakash, G. K.; Olah, G. A. J. Am. Chem. Soc. 1980, 102, 683.
33. (b) Dutler, R.; Rauk, A.; Withworth, S. M.; Sorensen, T. S. J. Am. Chem. Soc. 1991, 113, 411.
34. (c) Gomann, K.; Herpers, E.; Kirmse, W. Eur. J. Org. Chem. 1998, 2245.
35. (a) Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
36. (b) Bartoli, G.; Marcatoni, E.; Petrini, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1061.
37. (c) Dimitrov, V.; Bratovanov, S.; Simova, S.; Kostova, K. Tetrahedron Lett. 1994, 35, 6713.
38. (d) Dimitrov, V.; Kostova, K.; Genov, M. Tetrahedron Lett. 1996, 37, 6787.
39. 2 as eluent to afford 0.415 g (80%) of 1-hydroxymethyl-3-methyl-2-oxaadamantane (2).
40. 3 only method A could be applied, the sensitivity of vinyl magnesium bromide plays the main role for the lower yield.
41. Results to be published.