A new route to eremophilanes: synthesis of (±)-eremophilenolide, (±)-eremophiledinone, and (±)-deoxyeremopetasidione

Tetrahedron Letters

Volumn 49, Issue 42, 2008, Pages 6084-6086

  Srinivas, P ^a,b   Srinivasa Reddy, D ^a   Shiva K , Kyasa ^a   Dubey, P K ^b   Iqbal, Javed ^a   Das, Parthasarathi ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JNTUH COLLEGE OF ENGINEERING   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYEREMOPETASIDIONE; EREMOPHILEDINONE; EREMOPHILENOLIDE; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GRIGNARD REACTION; HYDROLYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ALNUS;

EID: 50649111859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.006     Document Type: Article

References (39)

1. Merritt A.T., and Ley S.V. Nat. Prod. Rep. 9 (1992) 243
2. Ley S.V., Denholm A.A., and Wood A. Nat. Prod. Rep. 10 (1993) 109
3. Hanson J.R. Nat. Prod. Rep. 16 (1999) 209
4. General reviews on eremophilanes:. Faulkner D.J. Nat. Prod. Rep. 19 (2002) 1
5. Fraga B.M. Nat. Prod. Rep. 19 (2002) 650
6. Synthesis of eremophilanes and related compounds: (a) Fisher, N. H.; Oliver, E. J.; Fisher, H. D. In Progress in the Chemistry of Organic Natural Products; Herz, W.; Grisebach, H. K.; Eds., G. W. Spinger: New York, 1979; Vol. 38, Chapter 2.
7. Prasad C.V.C., and Chan T.H. J. Org. Chem. 52 (1987) 120
8. Srikrishna A., Nagaraju S., Venkateswarlu S., Hiremath U.S., Reddy T.J., and Venugopalan P. J. Chem. Soc., Perkin Trans. 1 (1999) 2069
9. Srikrishna A., and Reddy T.J. Arkivoc viii (2001) 9
10. Silva Jr. L.F. Synthesis (2001) 671
11. Back T.G., Nava-Salgado V.O., and Payne J.E. J. Org. Chem. 66 (2001) 4361
12. Brocksom T.J., Coelho F., Depres J.P., Green A.E., Freire de Lima M.E., Hamelin O., Hartmann B., Kanazawa A.M., and Wang Y. J. Am. Chem. Soc. 124 (2002) 15313
13. Mehta G., and Senthil Kumaran R.S. Tetrahedron Lett. 44 (2003) 7055
14. Reddy D.S., and Kozmin S.A. J. Org. Chem. 69 (2004) 4860
15. Isolation of eremophilenolides:. Sugama K.O., Hayashi K., and Mitsuhashi H. Phytochemistry 24 (1985) 1531
16. Georges M., Jean-Marc N., Lousiette L.M.-O., Paul A., Abdelhamid B., and Abdessmed K. Phytochemistry 29 (1990) 2207
17. Paul A., Abdelhamid B., Georges M., and Lousiette L.M.-O. Phytochemistry 30 (1991) 2083
18. Wang W., Gao K., and Jia Z. J. Nat. Prod. 65 (2002) 714
19. Synthetic approaches for eremophilenolides:. Nagakura I., Maeda S., Ueno M., Funamizu M., and Kitahara Y. Chem. Lett. (1975) 1143
20. Miyashita T.M., Kumazawa T., and Yishikoshi A. Chem. Lett. (1979) 163
21. Acobi P.A., Craig T.A., Walker D.G., Arrick B.A., and Frechette R.F. J. Am. Chem. Soc. 106 (1984) 4450
22. Laura H.M., Shanmugham M.S., White J.D., and Drew M.G.B. Org. Biomol. Chem. 4 (2006) 1020
23. Isolation and synthesis of eremopetasidione: (a) Dictionary of chinese Meteria Medica; Shanghai Scientific Technological Publishers and Shougakukun; Shougakukun, Tokyo, 1985, p 2386.
24. Yaoita Y.-F., and Kikuchi M. Phytochemistry 37 (1994) 1765
25. Hsu D.-S., Hsu P.-Y., and Liao C.-C. Org. Lett. 3 (2001) 263
26. Dakoji S., Shin I., Becker D.F., Stankovich M.T., and Liu H.-w. J. Am. Chem. Soc. 118 (1996) 10971
27. 4, and evaporated in vacuum.
28. Reddy D.S. Org. Lett. 6 (2004) 3345
29. Reddy D.S., Palani K., Balasubrahmanyam D., Vijju K.V.B., and Iqbal J. Tetrahedron Lett. 46 (2005) 5211
30. Eliel E.L., Clawson L., and Knox D.E. J. Org. Chem. 50 (1985) 2707
31. Somers P.K., Wandless T.J., and Schreiber S.L. J. Am. Chem. Soc. 113 (1991) 8045
32. Boons G.-J., Clase J.A., Lennon I.C., Ley S.V., and Staunton J. Tetrahedron 51 (1995) 5417
33. Naya L., Matsumoto T., Makiyama M., and Tsumura M. Heterocycles 10 (1978) 177
34. + 265.1804, found 265.1801.
35. + 235.1698, found 235.1700.
36. +.
37. Tang Q., and Sen S.E. Tetrahedron Lett. 39 (1998) 2249
38. Edwards J.A., Calzada M.C., Ibanez L.C., Rivera M.E.C., Urquiza R., Cardona L., Orr J.C., and Bowers A. J. Org. Chem. 29 (1964) 3481
39. + 221.1547, found 221.1551.