Formation of novel polycyclic cage compounds through 'uncaging' of readily accessible higher cage compounds

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5775-5779

  James, Beena ^a   Rath, Nigam P ^b   Suresh, E ^c   Nair, Mangalam S ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^c CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 5 METHYL 8 METHYLENE 6 OXOTRICYCLO[5.3.0.0 3,9 ]DECANE 4 CARBOXYLIC ACID; 2 BROMO 5 METHYL 8 METHYLENE 6 OXOTRICYCLO[5.3.0.0 3,9 ]DECANE 4 METHYLCARBOXYLATE; 3 CHLOROMETHYL 4 (CARBOMETHOXY)TETRACYCLO[4.2.1.1 3,8 .0 2,5 ]DECA 7(11) EN 10 ONE; 7 BROMOMETHYL 8 (CARBOMETHOXY)TETRACYCLO[4.2.1.1. 4,7 .0 2,5 ]DECA 3(11) EN 10 ONE; 7 CHLOROMETHYL 8 (CARBOMETHOXY)TETRACYCLO[4.2.1.1 4,7 .0 2,5 ]DECA 3(11) EN 10 ONE; METHYL 4 METHYLENE 6 OXOPENTACYCLO[5.4.0.0 2,5 .0 3,10 .0 7,9 ]UNDECANE 9 CARBOXYLATE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG HYDROLYSIS; DRUG SYNTHESIS; ORGANIC CHEMISTRY; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 33745931397     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.005     Document Type: Article

References (37)

1. Kruger H.G., Martins F.J.C., and Viljoen A.M. J. Org. Chem. 69 (2004) 4863
2. Mehta G., and Vidya R. J. Org. Chem. 65 (2000) 3497
3. Marchand A.P. Aldrichim. Acta 28 (1995) 95
4. Osawa E., and Yonemitsu O. Carbocyclic Cage Compounds (1992), VCH, New York, NY
5. Marchand A.P. Synlett (1991) 73
6. Marchand A.P., Arney Jr. B.E., and Dave P.R. J. Org. Chem. 53 (1988) 443
7. Marchand A.P., Dave P.R., Rajapaksa D., Arney Jr. B.E., Flippen-Anderson J.L., Gilardi R., and George C. J. Org. Chem. 54 (1989) 1769
8. Gedenhuys W.J., Malan S.F., Bloomquist J.R., Marchand A.P., and Van der Schyf C. J. Med. Res. Rev. 25 (2005) 21
9. Eaton P.E. Angew. Chem., Int. Ed. Engl. 31 (1992) 1421
10. Michalson E.T., and Sqmurzkoviez J. Prog. Drug. Res. 33 (1989) 135
11. Grobler E., Grobler A., Van der Schyf C.J., and Malan S.F. Bioorg. Med. Chem. 14 (2006) 1176
12. Geldenhuys W.J., Malan S.F., Muruges T., Van der Schyf C.J., and Bloomquist J.R. Bioorg. Med. Chem. 12 (2004) 1799
13. Zah J., Blanche G.T., Erasmus E., and Malan S.F. Bioorg. Med. Chem. 11 (2003) 3569
14. Gante J. Angew. Chem., Int. Ed. Engl. 33 (1994) 1699
15. Giannis A., and Kolter T. Angew. Chem., Int. Ed. Engl. (1993) 1267
16. Mehta G., and Srikrishna A. Chem. Rev. 97 (1997) 671
17. Mehta G., and Reddy A.V. J. Chem. Soc., Chem. Commun. (1984) 1058
18. Mehta G., Reddy D.S., and Reddy A.V. Tetrahedron Lett. 25 (1984) 2275
19. Mehta G., Rao K.S., Marchand A.P., and Kaya R. J. Org. Chem. 49 (1984) 3848
20. Mehta G., and Reddy A.V. J. Chem. Soc., Chem. Commun. (1981) 756
21. Marchand A.P., Chong H.S., Shukla R., Sharma G.V.M., Kumar K.A., Zope U.R., and Bott S.G. Tetrahedron 52 (1996) 13531
22. Martins F.J.C., Viljoen A.M., Coetzee M., Fourie L., and Wessels P.L. Tetrahedron 47 (1991) 9215
23. Marchand A.P., Aavula B.R., and Bott S.G. Tetrahedron 54 (1998) 5105
24. Chow T.J., and Wu T.-K. J. Org. Chem. 56 (1991) 6833
25. Marchand A.P., LaRoe W.D., Sharma G.V.M., Suri S.C., and Reddy D.S. J. Org. Chem. 51 (1986) 1622
26. Craze G.A., and Watt I. J. Chem. Soc., Perkin Trans. 2 (1981) 175
27. Marchand A.P., Huang C., Kaya R., Baker A.D., Jemmis E.D., and Dixon D.A. J. Am. Chem. Soc. 107 (1987) 7095
28. Marchand A.P., Kaya R., and Baker A.D. Tetrahedron Lett. 25 (1984) 795
29. Cookson R.C., Crundwell E., Hill R.R., and Hudec J. J. Chem. Soc. (1964) 3062
30. Nair M.S., Sudhir U., Joly S., and Rath N.P. Tetrahedron 55 (1999) 7653
31. Suri S.C. J. Org. Chem. 58 (1993) 4153
32. Suri S.C., and Hardcastle K.I. J. Org. Chem. 57 (1992) 6357
33. Suri S.C. Tetrahedron Lett. 31 (1990) 3695
34. Nair M.S., Sudhir U., and Rath N.P. Tetrahedron 57 (2001) 7749
35. -1.
36. -1; GOF = 1.046; R indices (I > 2σ): R1 = 0.0483, wR2 = 0.1352.The crystal structures for compounds 3 and 5 have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers 600719 and 600349, respectively.
37. 3,9]decane-4-carboxylic acid (8): Yield: 35%; crystallized from dichloromethane-petroleum ether (1:4).