Cyclopropylcarbinyl radicals as three-carbon insertion units: Easy synthesis of C-15 macrocyclic ketones by three-carbon ring expansion

Tetrahedron Letters

Volumn 45, Issue 26, 2004, Pages 5143-5145

  Rüedi, Georg ^a   Hansen, Hans Jürgen ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Cyclopropylcarbinyl radicals; Musk odorants; Rearrangement; Ring expansion; Vacuum pyrolysis

Indexed keywords

CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE; MACROCYCLIC COMPOUND; METHANOL DERIVATIVE;

ARTICLE; HIGH TEMPERATURE; ISOMERIZATION; SYNTHESIS;

INSERTION SEQUENCES;

EID: 2942568050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.148     Document Type: Article

References (35)

1. Ohloff G. Riechstoffe und Geruchssinn. Die molekulare Welt der Düfte. 1990;Springer, Berlin
2. For pertinent reviews, see: Fräter G., Bajgrowicz J.A., Kraft P. Tetrahedron. 54:1998;7633
3. Williams A.S. Synthesis. 1999;1707
4. Fráter G., Bajgrowicz J.A., Denis C., Kraft P. Angew. Chem., Int. Ed. 39:2000;2980
5. Rüedi G., Nagel M., Hansen H.-J. Org. Lett. 5:2003;4211
6. A similar three-carbon ring expansion had earlier been observed when 2-cyclopropylcyclohexanone was irradiated, see: Carlson R.G., Biersmith E.L. J. Chem. Soc., Chem. Commun. 1969;1049
7. McMillen D.F., Golden D.M. Annu. Rev. Phys. Chem. 33:1982;493
8. Walton J.C. Magn. Reson. Chem. 25:1987;998
9. Curtiss L.A., Raghavachari K., Trucks G.W., Pople J.A. J. Phys. Chem. 94:1990;7221
10. Smith D.M., Nicolaides A., Golding B.T., Radom L. J. Am. Chem. Soc. 120:1998;10223
11. Halgren T.A., Roberts J.D., Horner J.H., Martinez F.N., Tronche C., Newcomb M. J. Am. Chem. Soc. 122:2000;2988
12. For pertinent examples see: Kochi J.K., Krsic P.J., Eaton D.R. J. Am. Chem. Soc. 91:1969;1877
13. Effio A., Griller D., Ingold K.U., Beckwith A.L.J., Serelis A.K. J. Am. Chem. Soc. 102:1980;1734
14. Newcomb M., Glenn A.G. J. Am. Chem. Soc. 111:1989;275
15. Newcomb M. Tetrahedron. 49:1993;1151
16. Beckwith A.L.J., Bowry V.W. J. Am. Chem. Soc. 116:1994;2710
17. Martinez F.N., Schlegel H.B., Newcomb M. J. Org. Chem. 61:1996;8547
18. Martinez F.N., Schlegel H.B., Newcomb M. J. Org. Chem. 63:1998;3618
19. Choi S.-Y., Horner J.H., Newcomb M. J. Org. Chem. 65:2000;4447
20. Horner J.H., Newcomb M. J. Am. Chem. Soc. 123:2001;4364
21. Cooksy A.L., King H.F., Richardson W.H. J. Org. Chem. 68:2003;9441
22. Newcomb M., Miranda N. J. Am. Chem. Soc. 125:2003;4080
23. 3): δ 209.3, 137.3, 137.2, 135.5, 135.4, 130.8, 130.5, 114.5, 114.3, 43.8, 32.5, 32.3, 29.8, 29.6, 29.38, 29.35, 29.34, 29.30, 29.13, 29.08, 23.8
24. We thank Givaudan Research Ltd. Dübendorf (Switzerland) for expert olfactory evaluation
25. The introduction of a (Z)-double bond could also be accomplished when a threefold excess of a 1:1 mixture of (E/Z)-1-propenyl lithium was employed
26. Davies A.G., Godet J.-Y., Muggleton B., Pereyre M. J. Chem. Soc., Chem. Commun. 1976;813
27. Davies A.G., Muggleton B., Godet J.-Y., Pereyre M., Pommier J.-C. J. Chem. Soc., Perkin. Trans. 2. 1976;1719
28. Castaing M., Pereyre M., Ratier M. J. Chem. Soc., Perkin. Trans. 2. 1979;287
29. Mariano P.S., Bay E. J. Org. Chem. 45:1980;1763
30. Bowry V.W., Lusztyk J., Ingold K.U. J. Am. Chem. Soc. 113:1991;5687
31. Choi S.-C., Newcomb M. Tetrahedron. 51:1995;657
32. Takekawa Y., Shishido K. J. Tetrahedron Lett. 40:1999;6817
33. Takekawa Y., Shishido K. J. Org. Chem. 66:2001;8490
34. Compound 8 had earlier been synthesized through annelation-fragmentation (a) and macrocyclization (b), see: Fehr C. Helv. Chim. Acta. 66:1983;2512
35. Fujimoto S., Yoshikawa K., Itoh M., Kitahara T. Biosci. Biotechnol. Biochem. 66:2002;1389