β-Hydroxy-α-tosyloxy esters as chiral building blocks for the enantioselective synthesis of benzo-annulated oxa-heterocycles: scope and limitations

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4162-4173

  Das, Sajal Kumar ^a   Panda, Gautam ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 HYDROXY 1 METHYL ETHYL) 1,2 DIHYDRONAPHTHO[2,1 B]FURAN 1 OL; 2 (1 HYDROXY 1 METHYL ETHYL) 2,3 DIHYDROBENZOFURAN 3 OL; BENZOPYRAN DERIVATIVE; BETA HYDROXY ALPHA TOSYLOXY ESTER DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS;

EID: 41549104831     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.001     Document Type: Article

References (45)

1. For recent reviews, see:
2. Weber L. Curr. Opin. Chem. Biol. 4 (2000) 295
3. Wessjohann L.A. Curr. Opin. Chem. Biol. 4 (2000) 303
4. Hall D.G., Manku S., and Wang F. J. Comb. Chem. 3 (2001) 125
5. Ganesan A. Pure Appl. Chem. 73 (2001) 1033
6. Breinbauer R., Vetter I.R., and Waldmann H. Angew. Chem., Int. Ed. 41 (2002) 2878
7. Schreiber S.L. Science 287 (2000) 196
8. Abel U., Koch C., Speitling M., and Hansske F.G. Curr. Opin. Chem. Biol. 6 (2002) 453
9. Liao Y., Hu Y., Wu J., Zhu Q., Donovan M., Fathi R., and Yang Z. Curr. Med. Chem. 10 (2003) 2285
10. Burke M.D., and Schreiber S.L. Angew. Chem., Int. Ed. 43 (2004) 46
11. Kim Y., Arai M.A., Arai T., Lamenzo J.O., Dean III E.F., Patterson N., Clemons P.A., and Schreiber S.L. J. Am. Chem. Soc. 126 (2004) 14740
12. Ortholand J.Y., and Ganesan A. Curr. Opin. Chem. Biol. 8 (2004) 271
13. Boldi A.M. Curr. Opin. Chem. Biol. 8 (2004) 281
14. Tan D.S. Comb. Chem. High Throughput Screening 7 (2004) 631
15. Mishra J.K., and Panda G. J. Comb. Chem. 9 (2007) 321
16. Mishra J.K., and Panda G. Synthesis (2005) 1881
17. Mishra J.K., Garg P., Dohare P., Kumar A., Siddiqi M.I., Ray M., and Panda G. Bioorg. Med. Chem. Lett. 17 (2007) 1326
18. Ishii H., Ishikawa T., Sekiguchi H., and Hosoya K. Chem. Pharm. Bull. 21 (1973) 2346
19. Asahara T., Sakakibara I., Okuyama T., and Shibata S. Planta Med. 50 (1984) 488
20. Alami I., Clerivet A., Naji M., Van Munster M., and Macheix J.J. Phytochemistry 51 (1999) 733
21. Rajendran K., Mesta C.K., Paknikar S.K., and Bhattacharyya S.C. Indian J. Chem. 8 (1970) 200
22. Takashima J., and Ohsaki A. J. Nat. Prod. 65 (2002) 1843
23. Yin S., Fan C., Wang Y., Dong L., and Yue J. Bioorg. Med. Chem. 12 (2004) 4387
24. Ito C., Katsuno S., Kondo Y., Tan H.T., and Furukawa H. Chem. Pharm. Bull. 48 (2000) 339
25. Itoigawa M., Ito C., Tan H.T., Okuda M., Tokuda H., Nishino H., and Furukawa H. Cancer Lett. 174 (2001) 135
26. Jarvis B.B., Pena N.B., Comezoglu S.N., and Rao M.M. Phytochemistry 25 (1986) 533
27. Macias F.A., Varela R.M., Torres A., Molinillo J.M.G., and Fronczek F.R. Tetrahedron Lett. 34 (1993) 1999
28. Macias F.A., Molinillo J.M.G., Varela R.M., Torres A., and Fronczek F.R. J. Org. Chem. 59 (1994) 8261
29. Zhang J., Wang X., Wang W., Quan W., She X., and Pan X. Tetrahedron 63 (2007) 6990
30. Fleming P.R., and Sharpless K.B. J. Org. Chem. 56 (1991) 2869
31. Chandrasekhar S., Sultana S.S., Kiranmai N., and Narsihmulu C. Tetrahedron Lett. 48 (2007) 2773
32. Pearson A.J., and Heo J.-N. Tetrahedron Lett. 41 (2000) 5991
33. Chun J., He L., and Bittman R. J. Org. Chem. 65 (2000) 7634
34. Luzzio F.A., Thomas E.M., and Figg W.D. Tetrahedron Lett. 41 (2000) 7151
35. Boger D.L., and Schule G. J. Org. Chem. 63 (1998) 6421
36. Rao A.V.R., Chakraborty T.K., Reddy K.L., and Rao A.S. Tetrahedron Lett. 35 (1994) 5043
37. Rao A.V.R., Rao S.P., and Bhanu M.N. J. Chem. Soc., Chem. Commun. (1992) 859
38. Ziegler F.E., and Wang Y. J. Org. Chem. 63 (1998) 7920
39. Gogoi S., Barua N.C., and Kalita B. Tetrahedron Lett. 45 (2004) 5577
40. Khadem S., Joseph R., Rastegar M., Leek D.M., Oudatchin K.A., and Arya P. J. Comb. Chem. 6 (2004) 724
41. Zou Y., Lobera M., and Snider B.B. J. Org. Chem. 70 (2005) 1761
42. Snider B.B., and Wu X. Heterocycles 70 (2006) 279
43. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483
44. Chang C.-Y., Kuo S.-C., Lin Y.-L., Wang J.-P., and Huang L.-J. Bioorg. Med. Chem. Lett. 14 (2004) 2797
45. Quideau S., Pouysegu L., Oxoby M., and Looney M.A. Tetrahedron 57 (2001) 319