Synthesis of a novel, bowl-like bis γ-lactone

Tetrahedron Letters

Volumn 48, Issue 2, 2007, Pages 207-209

  Khan, Faiz Ahmed ^a   Dwivedi, Vineet ^a   Rout, Bhimsen ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRACHLORO 5,5 DIMETHOXYCYCLOPENTADIENE; 2,5 DIHYDRO 2,5 DIMETHOXYFURAN; CYCLOPENTADIENE DERIVATIVE; FURAN DERIVATIVE; GAMMA LACTONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; DIELS ALDER REACTION; HYDROLYSIS; SYNTHESIS;

BETULACEAE;

EID: 33845207680     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.062     Document Type: Article

References (26)

1. Wu H.J., and Lin C.C. J. Org. Chem. 60 (1995) 7558-7566
2. Wu H.J., and Wu C.Y. Tetrahedron Lett. 38 (1997) 2493-2496
3. Mehta G., and Vidya R. Tetrahedron Lett. 38 (1997) 4173-4176
4. Mehta G., and Vidya R. J. Org. Chem. 66 (2001) 6905-6912
5. Geldenhuys W.J., Malan S.F., Murugesan T., Van der Schyf C.J., and Bloomquist J.R. Bioorg. Med. Chem. 12 (2004) 1799-1806
6. Mdzinarishvili A., Geldenhuys W.J., Abbruscato T.J., Bickel U., Klein J., and Van der Schyf C. Neurosci. Lett. 383 (2005) 49-53
7. Carreño M.C., Luzón C.G., and Ribagorda M. Chem. Eur. J. 8 (2002) 208-216 and references cited therein
8. Khan F.A., Prabhudas B., Dash J., and Sahu N. J. Am. Chem. Soc. 122 (2000) 9558-9559
9. Khan F.A., and Sahu N. J. Catal. 231 (2005) 438-442
10. Khan F.A., and Dash J. J. Am. Chem. Soc. 124 (2002) 2424-2425
11. Khan F.A., and Dash J. J. Org. Chem. 68 (2003) 4556-4559
12. Khan F.A., Dash J., and Rout B. Tetrahedron Lett. 45 (2004) 9285-9288
13. Khan F.A., Satapathy R., Dash J., and Savitha G. J. Org. Chem. 69 (2004) 5295-5301
14. Khan F.A., Dash J., Sudheer Ch., Sahu N., and Parasuraman K. J. Org. Chem. 70 (2005) 7565-7577
15. Khan F.A., and Rout B. Tetrahedron Lett. 47 (2006) 5251-5253
16. Khan F.A., Sahu N., Dash J., and Prabhudas B. J. Indian Inst. Sci. 81 (2000) 325-331
17. Khan F.A., Dash J., Sahu N., and Sudheer Ch. J. Org. Chem. 67 (2002) 3783-3787
18. Khan F.A., and Rao C.N. Tetrahedron Lett. 47 (2006) 7567-7570
19. Smith III A.B., and Scarborough Jr. R.M. Synth. Commun. 10 (1980) 205-211
20. Plietker B. Synthesis (2005) 2453-2472
21. Fell S.C.M., and Harbridge J.B. Tetrahedron Lett. 31 (1990) 4227-4228
22. Cecchini C., Mico A.D., D'Onofrio F., Piancatelli G., and Tofani D. Tetrahedron Lett. 34 (1993) 7101-7104
23. For an isolated example of a Diels-Alder adduct of 5 with a related diene, see:. Chang W.-H. J. Chem. Soc. (1965) 2305-2312 Except for an mp and elemental analysis, no spectral data or stereochemistry were reported
24. For a review on synthetic applications of diene 6, see:. Khan F.A., Prabhudas B., and Dash J. J. Prakt. Chem. 342 (2000) 512-517
25. The structure was solved using sir92 (a) and refined using shelxl97 (b):. Altomare A., Gascarano G., Giacovazzo C., and Guagliardi A. J. Appl. Crystallogr. 26 (1993) 343-350
26. Sheldrick, G. M. shelxl97. Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997. Crystallographic data (excluding structure factors) for 4 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 622417. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk.