A short and efficient synthesis of (±)-β-cuparenone

Tetrahedron Letters

Volumn 47, Issue 18, 2006, Pages 3027-3029

  Kulkarni, Mukund G ^a   Davawala, Saryu I ^a   Shinde, Mahadev P ^a   Dhondge, Attrimuni P ^a   Borhade, Ajit S ^a   Chavhan, Sanjay W ^a   Gaikwad, Dnyaneshwar D ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CUPARENONE;

ARTICLE; CLAISEN REARRANGEMENT; OLEFINATION; SYNTHESIS; WITTIG REACTION;

EID: 33645858277     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.012     Document Type: Article

References (105)

1. Chetty G.L., and Dev S. Tetrahedron Lett. (1964) 73-77
2. Tomita B., Hirose Y., and Nakatsuka T. Tetrahedron Lett. 7 (1968) 843-848
3. Matsuo A., Nakayama N., and Nakayama M. Phytochemistry 24 (1985) 777-781
4. Anand R.C., and Ranjan H. Ind. J. Chem. 23B (1984) 1054-1057
5. Asaoka M., Takenouchi K., and Taket H. Tetrahedron Lett. 29 (1988) 325-328
6. Honda T., Kimura N., and Tsubuki M. Tetrahedron: Asymmetry 4 (1993) 21-24
7. Chavan S.P., Ravindranathan T., Patil S.S., Dhondage V.D., and Dantale S.W. Tetrahedron Lett. 37 (1996) 2629-2630
8. Kametani T., Kawamura K., Tsubuki M., and Honda T. Chem. Pharm. Bull. 33 (1985) 4821-4828
9. Meyers A.I., and Lefker B.A. J. Org. Chem. 1 (1986) 1541-1544
10. Green A.E., Charbonnier F., Luche M.J., and Moyano A. J. Am. Chem. Soc. 109 (1987) 4752-4753
11. Eilbracht P., Balb E., and Acker M. Tetrahedron Lett. 25 (1984) 1131-1132
12. Eilbracht P., Balb E., and Acker M. Chem. Ber. 118 (1985) 825-829
13. Taber D.F., Petty E.H., and Raman K. J. Am. Chem. Soc. 107 (1985) 196-199
14. Posner G.H., Kogan Y.P., and Hulce M. Tetrahedron Lett. 25 (1984) 383-386
15. Anand R.C., and Ranjan H. Ind. J. Chem. 24B (1985) 673-674
16. Srikrishna A., and Krishnan G. Ind. J. Chem. 29B (1990) 879-880
17. Srikrishna A., and Sundarababu G. Tetrahedron 46 (1990) 3601-3606
18. Martin S.F., Phillips F.W., Puckette T.A., and Colapret J.A. J. Am. Chem. Soc. 102 (1980) 5866-5872
19. Acherar S., Audran G., Cecchin F., and Monti H. Tetrahedron 60 (2004) 5907-5912
20. Walter M.A., Hoem A.B., Archand H.R., Hegeman A.D., and McDonough C.S. Tetrahedron Lett. 34 (1993) 1453-1456
21. Fadel A., Canet J.L., and Salaün J. Synlett 1 (1991) 60-62
22. Canet J.L., Fadel A., and Salaün J. J. Org. Chem. 57 (1992) 3463-3473
23. Asaoka M., Shima K., and Takei H. Tetrahedron Lett. 28 (1987) 5669-5672
24. Aavula B.R., Cui Q., and Mash E.A. Tetrahedron: Asymmetry 11 (2000) 4681-4686
25. Mayers A.I. In: Trost B.M. (Ed). Stereocontrolled Organic Synthesis (1994), Blackwell 145-146
26. Gadwood R.C. J. Org. Chem. 48 (1983) 2098-2101
27. Laboureur J.L., and Kreif A. Tetrahedron Lett. 25 (1984) 2713-2716
28. Kreif A., and Laboureur J.L. Tetrahedron Lett. 28 (1987) 1545-1548
29. Halazy S., Zuttuman F., and Krief A. Tetrahedron Lett. 23 (1982) 4385-4388
30. Leriverend P.P. Bull. Soc. Chim. Fr. (1973) 3498-3501
31. Parker W., Ramage R., and Raphael R.A. J. Chem. Soc. (1962) 1558-1563
32. Nemoto H., Ishibashi H., Nagamochi M., and Fukumoto K. J. Org. Chem. 57 (1992) 1707-1712
33. Kanada K., Kii N., Jitsukawa K., and Teranishi S. Tetrahedron Lett. 22 (1981) 2595-2597
34. Hayakawa Y., Shimizu F., and Noyori R. Tetrahedron Lett. 11 (1978) 993-994
35. Takano S., Inomata K., and Ogasawara K. J. Chem. Soc., Chem. Commun. 5 (1989) 271-272
36. Gharpure M.M., and Rao A.S. Synth. Commun. 19 (1989) 679-688
37. Wenkert E., Buckwalter B.L., Craveiro A.A., Sanchez E.L., and Sathe S. J. Am. Chem. Soc. 100 (1978) 1267-1273
38. Gharpure M.M., and Rao A.S. Synth. Commun. 19 (1989) 1813-1823
39. Nakatani H., Suso T., Ishibashi H., and Ikeda M. Chem. Pharm. Bull. 38 (1990) 1233-1237
40. Sakurai H., Shirahata A., and Hosomi A. Angew. Chem., Int. Ed. Engl. 18 (1979) 163-166
41. Okano K., Suemune H., and Sakai K. Chem. Pharm. Bull. 36 (1988) 1379-1385
42. Aavula B.R., Cui Q., and Mash E.A. Tetrahedron: Asymmetry 11 (2000) 4681-4686
43. Acherar S., Audran G., Cecchin F., and Monti H. Tetrahedron 60 (2004) 5907-5912
44. Takano S., Moriya M., and Ogasawara K. Tetrahedron Lett. 33 (1992) 329-332
45. Castro J., Moyano A., Pericas M.A., Riera A., Greene A.E., Alvarez-Larena A., and Piniella J.F. J. Org. Chem. 61 (1996) 9016-9020
46. Lansbury P.T., and Hilfiker F.R. J. Chem. Soc. D 11 (1969) 619-620
47. Mane R.B., and Rao G.S.K. J. Chem. Soc., Perkin Trans. 1 16 (1973) 1806-1808
48. Casares A., and Maldonado L.A. Synth. Commun. 6 (1976) 11-16
49. Jung M.E., and Radcliffe C.D. Tetrahedron Lett. 21 (1980) 4397-4400
50. Halazy S., Zutterman F., and Krief A. Tetrahedron Lett. 23 (1982) 4385-4388
51. Paquette L.A., Fristad W.E., Dime D.S., and Bailey T.R. J. Org. Chem. 45 (1980) 3017-3028
52. Green A.E., Lansard J.P., Luche J.L., and Petrier C. J. Org. Chem. 49 (1984) 931-932
53. Ishibashi H., Nakatani H., Choi D.J., Taguchi M., and Ikeda M. Chem. Pharm. Bull. 38 (1990) 1738-1739
54. Srikrishna A., and Nagaraju S. Ind. J. Chem. Sect. B. 30B (1991) 1006-1009
55. Srikrishna A., and Reddy T.J. Tetrahedron 54 (1998) 8133-8140
56. Srikrishna A., and Sundarababu G. Tetrahedron 47 (1991) 481-496
57. Srikrishna A., and Krishnan K. Tetrahedron 48 (1992) 3429-3436
58. Green A.E., Charbonnier F., Luche M.J., and Moyano A. J. Am. Chem. Soc. 109 (1987) 4752-4753
59. Gharpure M.M., and Rao A.S. Synth. Commun. 19 (1989) 679-686
60. Fadel A., Canet J.L., and Salaun J. Synlett 1 (1991) 60-62
61. Canet J.L., Fadel A., and Salaun J. J. Org. Chem. 57 (1992) 3463-3473
62. Okano K., Suemune H., and Sakai K. Chem. Pharm. Bull. 36 (1988) 1379-1385
63. Asaoka M., Hayashibe S., Sonada S., and Takei H. Tetrahedron Lett. 31 (1990) 4761-4764
64. Sato T., Hayashi M., and Hayata T. Tetrahedron 48 (1992) 4099-4114
65. Satoh T., Yoshida M., Takahashi Y., and Ota H. Tetrahedron: Asymmetry 14 (2003) 281-288
66. Kuwahara S., and Saito M. Tetrahedron Lett. 45 (2004) 5047-5049
67. Paul T., Pal A., and Mukherjee D. ARKIVOC (2003) 104-114
68. Saito M., and Kuwahara S. Biosci., Biotechnol., Biochem. 69 (2005) 374-381
69. Xaho X.Z., Jia Y.X., and Tu Y.Q. J. Chem. Res. (S) 2 (2003) 54-55
70. Grainger R.S., and Patel A. Chem. Commun. 9 (2003) 1072-1073
71. Kametani T., Tsubuki M., and Nemoto H. J. Chem. Soc., Perkin Trans. 1 (1980) 759-761
72. Kametani T., Tsubuki M., and Nemoto H. Heterocycles 12 (1979) 791-793
73. Dauben W.G., and Oberhansli P. J. Org. Chem. 31 (1966) 315-317
74. Nayek A., Drew M.G.B., and Ghosh S. Tetrahedron 59 (2003) 5175-5181
75. Bovicelli P., and Mincione E. Synth. Commun. 18 (1988) 2037-2050
76. Bailey W.F., and Khanolkar A.D. Tetrahedron 47 (1991) 7727-7738
77. Abad A., Agullo C., Arno M., Cunat A.C., Garcia M., Teresa Z., and Ramon J. J. Org. Chem. 61 (1996) 5916-5919
78. Ho T.-L., and Chang M.-H. J. Chem. Soc., Perkin Trans. 1 (1999) 2479-2482
79. Mandelt K., and Fitjer L. Synthesis 10 (1998) 1523-1526
80. Parker W., Ramage R., and Raphael R.A. J. Chem. Soc. (1962) 1558-1563
81. Nakatani H., So T., Ishibashi H., and Ikeda M. Chem. Pharm. Bull. 38 (1990) 1233-1237
82. Krief A., Laboureur J.L., Hobe M., and Barbeaux P. Studies Nat. Prod. Chem. 8 (1991) 3-14
83. Krief A., and Barbeaux P. Synlett 9 (1990) 511-514
84. Favaloro F.G., Goudreau C.A., Mundy B.P., Poon T., Slobodzian S.V., and Jensen B.L. Synth. Commun. 31 (2001) 1847-1855
85. Bovicelli P., and Mincione E. Synth. Commun. 18 (1988) 2037-2050
86. Ishibashi H., So T.S., Nakatani H., Minami K., and Ikeda M. J. Chem. Soc., Chem. Commun. 12 (1988) 827-828
87. Kametani T., Kawamura K., Tsubuki M., and Honda T. J. Chem. Soc., Perkin Trans. 1 (1988) 193-199
88. Schuda P.F., and Potlock S.J. Tetrahedron 43 (1987) 463-468
89. Potlock S.J. Diss. Abstr. Int. B 46 (1986) 3452-3453
90. Takeshita H., Mori A., and Nakamura S. Bull. Chem. Soc. Jpn. 57 (1984) 3152-3155
91. Kametani T., Kawamura K., Tsubuki M., and Honda T. J. Chem. Soc., Perkin Trans. 1 (1984) 1305-1310
92. Kametani T., Tsubuki M., and Nemoto H. Heterocycles 12 (1979) 791-793
93. Vijaysarathi P.R., and Rao G.S.K. Ind. J. Chem., Sect. B 15B (1977) 530-532
94. De Mayo P., and Suau R. J. Chem. Soc., Perkin Trans. 1 (1974) 2559-2561
95. Bird C.W., Yeong Y.C., and Hudec J. Synthesis 1 (1974) 27-28
96. Vig O.P., Parti R.K., Gupta K.C., and Bhatia M.S. Ind. J. Chem. 11 (1973) 981-982
97. Cohen T., Kreethadumrongdat T., Liu X., and Kulkarni V. J. Am. Chem. Soc. 123 (2001) 3478-3483
98. Bizier, N.; Brooks, A.; Mundy, B. P.; Poon, T. ACS National Meeting, San Diego, CA, United States, April 1-5, 2001.
99. Parker W., Ramage R., and Raphael R.A. Proc. Chem. Soc. (1961) 74
100. Srikrishna A., and Rao M.S. Synlett (2004) 374-376
101. Kulkarni M.G., and Pendharkar D.S. Tetrahedron 53 (1997) 3167-3172
102. Schwab P., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 118 (1996) 100-110
103. Dias E.L., Nguyen S.T., and Grubbs R.H. J. Am. Chem. Soc. 119 (1997) 3887-3897
104. Charles A.B., and Randolph A.C. J. Org. Chem. 44 (1979) 2328-2329
105. John A.S., and Herbert C.B. J. Org. Chem. 46 (1981) 4599-4600