Lactones 23: Synthesis of cis-fused bicyclic hydroxy lactones with a p-menthane system

Tetrahedron Asymmetry

Volumn 16, Issue 12, 2005, Pages 2087-2097

  Dams, Iwona ^a   Białońska, Agata ^a   Ciunik, Zbigniew ^a   Wawrzeńczyk, Czesław ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; LACTONE DERIVATIVE; PULEGONE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIS ISOMER; CLAISEN REARRANGEMENT; CRYSTALLOGRAPHY; ENANTIOMER; EPOXIDATION; LACTONIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 20444395445     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.04.020     Document Type: Article

References (56)

1. H. Guth J. Agric. Food Chem. 45 1997 3022 3026
2. H. Guth Helv. Chim. Acta 79 1996 1559 1571
3. J.-M. Gaudin Tetrahedron 56 2000 4769 4776
4. A. Hinterholzer, and P. Schieberle Flav. Fragr. J. 13 1998 49 55
5. R. Näf, and A. Velluz Flav. Fragr. J. 13 1998 203 208
6. T. Jagella, and W. Grosch Z. Lebensm.-Unters. Forsch. A 209 1999 16 21
7. E. Brenna, C. Fuganti, and S. Serra Tetrahedron: Asymmetry 14 2003 1 42
8. I. Dams, A. Białońska, Z. Ciunik, and C. Wawrzeńczyk J. Agric. Food Chem. 52 2004 1630 1634
9. I. Dams, C. Wawrzeńczyk, and J. Kula Polish Patent Application PL-362879 Bull. Polish Patent Office 7 2004 26
10. I. Dams, C. Wawrzeńczyk, and J. Gibka Polish Patent Application PL-362878 Bull. Polish Patent Office 7 2004 26
11. I. Dams, A. Białońska, Z. Ciunik, and C. Wawrzeńczyk Eur. J. Org. Chem. 2004 2662 2668
12. J.N. Bilton, H.B. Broughton, P.S. Jones, S.V. Ley, Z. Lidert, E.D. Morgan, H.S. Rzepa, R.N. Sheppard, A.M.Z. Slawin, and D.J. Williams Tetrahedron 43 1987 2805 2815
13. H.B. Broughton, S.V. Ley, A.M.Z. Slawin, D.J. Williams, and E.D. Morgan J. Chem. Soc., Chem. Commun. 1986 46 47
14. J.H. Butterworth, and E.D. Morgan Chem. Commun. 1968 23 24
15. W. Kraus, M. Bokel, A. Klenk, and H. Pohnl Tetrahedron Lett. 26 1985 6435 6438
16. I. Kubo, Y.-W. Lee, V. Balogh-Nair, K. Nakanishi, and A. Chapya J. Chem. Soc., Chem. Commun. 1976 949 950
17. J. Nawrot, B. Drożdż, and M. Holub Herba Polonica 31 1985 209 213
18. J. Nawrot, J. Harmatha, and L. Nowotny Biochem. Syst. Ecol. 12 1984 99 101
19. V.J. Paul, P. Ciminiello, and W. Fenical Phytochem. 27 1988 1011 1014
20. K. Munakata Pure Appl. Chem. 42 1975 57 66
21. W.M. Daniewski, M. Gumułka, D. Przesmycka, K. Ptaszyńska, E. Błoszyk, and B. Drożdż Phytochem. 38 1995 1161 1168
22. H.H. Appel, R.P.M. Bond, and K.H. Overton Tetrahedron 19 1963 635 641
23. M. Szczepanik, M. Grabarczyk, A. Szumny, and C. Wawrzeńczyk J. Plant Protection Res. 43 2003 87 96
24. E. Paruch, Z. Ciunik, J. Nawrot, and C. Wawrzeńczyk J. Agric. Food Chem. 48 2000 4973 4977
25. E. Paruch, J. Nawrot, and C. Wawrzeńczyk Pest Manag. Sci. 57 2001 776 780
26. A. Halarewicz-Pacan, B. Gabryś, K. Dancewicz, and C. Wawrzeńczyk J. Plant Protection Res. 43 2003 133 142
27. Szczepanik, M.; Dams, I; Wawrzeńczyk, C. Environ. Entomol., submitted for publication.
28. I. Dams, C. Wawrzeńczyk, M. Szczepanik, B. Gabryś, and K. Dancewicz Polish Patent Application PL-366262 Bull. Polish Patent Office 18 2004 74
29. I. Dams, C. Wawrzeńczyk, M. Szczepanik, B. Gabryś, and K. Dancewicz Polish Patent Application PL-366261 Bull. Polish Patent Office 18 2004 73
30. Dams, I. PhD Thesis, Wrocław University of Technology, Poland, 2004.
31. R.M. Silverstein, R.G. Brownlee, T.E. Bellas, D.L. Wood, and L.E. Browne Science 159 1968 889 891
32. D.L. Wood, L.E. Browne, B. Ewing, K. Lindahl, W.D. Bedard, P.E. Tilden, K. Mori, G.B. Pitman, and P.R. Hughes Science 192 1976 896 898
33. R.G. Riley, R.M. Silverstein, and J.C. Moser Science 183 1976 760 762
34. J.H. Tumlinson, M.G. Klein, R.E. Doolittle, T.L. Ladd, and A.T. Proveaux Science 197 1977 789 792
35. Y. Kuwahara, K. Matsumoto, Y. Wada, and T. Suzuki Appl. Entomol. Zool. 26 1991 85 89
36. Y. Kuwahara, L.T.M. Yen, Y. Tominaga, K. Matsumoto, and Y. Wada Agric. Biol. Chem. 46 1982 2283 2291
37. J.H. Borden, L. Chong, J.A. McLean, K.N. Slessor, and K. Mori Science 192 1976 894 896
38. A. Mosandl, and M. Gessner Z. Lebensm.-Unters. Forsch. 187 1988 40 44
39. T.J. Leitereg, D.G. Guadagni, J. Harris, T.R. Mon, and R. Teranishi J. Agric. Food Chem. 19 1971 785 787
40. H.G. Haring, F. Rijkens, H. Boelens, and A. Van der Gen J. Agric. Food Chem. 20 1972 1018 1021
41. G. Ohloff, W. Giersch, K.H. Schulte-Elte, P. Enggist, and E. Demole Helv. Chim. Acta 63 1980 1582 1588
42. G. Ohloff, B. Maurer, B. Winter, and W. Giersch Helv. Chim. Acta 66 1983 192 217
43. A. Mosandl, and C. Günther J. Agric. Food Chem. 37 1989 413 418
44. G. Beck Synlett 6 2002 837 850
45. A. Zaks, and D.R. Dodds Drug Discovery Today 2 1997 513 531
46. B.M. Kenyon, F. Browne, and R.J. D'Amato Exp. Eye Res. 64 1997 971 978
47. T.D. Stephens, C.J.W. Bunde, and B. Fillmore J. Biochem. Pharmacol. 59 2000 1489 1499
48. R.T. Brittain, G.M. Drew, and G.P. Levy Br. J. Pharmacol. 77 1982 105 114
49. E.H. Gold, W. Chang, M. Cohen, T. Baum, S. Ehrreich, G. Johnson, N. Prioli, and E.J. Sybertz J. Med. Chem. 25 1982 1363 1370
50. D.S. Tawfik, Z. Eshhar, A. Bentolia, and B.S. Green Synthesis 1993 968 972
51. T. Olejniczak, M. Grabarczyk, and C. Wawrzeńczyk J. Molecular Catal. B: Enzy. 11 2001 243 247
52. E. Paruch, Z. Ciunik, and C. Wawrzeńczyk Eur. J. Org. Chem. 1998 2667 2682
53. Dams, I.; Szczepanik, M.; Wawrzeńczyk, C. Polish Patent Application PL-370963, Bull. Polish Patent Office, in press.
54. Dams, I.; Szczepanik, M.; Wawrzeńczyk, C. Polish Patent Application PL-370964, Bull. Polish Patent Office, in press.
55. Oxford Diffraction, Poland Sp. z o.o., CrysAlis CCD and CrysAlis Red, V166, 2001.
56. Bruker AXS, SHELXTL V5.1, 1999.