An efficient aldol-based approach for the synthesis of dihydrokawain-5-ol

Tetrahedron Asymmetry

Volumn 20, Issue 16, 2009, Pages 1936-1939

  Kamal, Ahmed ^a   Reddy, Papagari Venkat ^a   Prabhakar, S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ETHYL ESTER; ALDEHYDE DERIVATIVE; DIHYDROKAWAIN; DIHYDROKAWAIN 5 OL; HYDROXYL GROUP; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIHYDROXYLATION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SHARPLESS EPOXIDATION; STEREOISOMERISM;

EID: 69749109774     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.08.006     Document Type: Article

References (45)

1. Argoudelis A.D., and Zieserl J.F. Tetrahedron Lett. 18 (1966) 1969-1973
2. Cavil G.W.K., Clark D.V., and Whitefield F.B. Aust. J. Chem. 21 (1968) 2819
3. Laurence B.R. J. Chem. Soc., Chem. Commun. (1982) 59
4. Honda T. J. Chem. Soc., Perkin Trans. 1 (1990) 1733
5. Wilkinson A.L., Hanefeld U., Wilkinson B., Leadlay P.F., and Staunton J. Tetrahedron Lett. 39 (1998) 9827-9830
6. Sato M., Nakashima H., Keisuke H., Hayashi M., Honzumi M., Taniguchi T., and Ogasawara K. Tetrahedron Lett. 42 (2001) 2833-2837
7. Hinterding K., Singhanat S., and Oberer L. Tetrahedron Lett. 42 (2001) 8463-8465
8. Wu Y., Shen X., Tang C.-J., Chen Z.L., Hu Q., and Shi W. J. Org. Chem. 11 (2002) 3802-3810
9. Yadav J.S., Reddy P.M.K., and Reddy P.V. Tetrahedron Lett. 48 (2007) 1037-1039
10. Chakraborty T.K., and Tapadar S. Tetrahedron Lett. 44 (2003) 2541-2543
11. Yamashita Y., Saito S., Ishitani H., and Kobayashi S. J. Am. Chem. Soc. 125 (2003) 3793-3798
12. Kobayashi S., Tsuchiya K., Harada T., Nishide M., Kurokawa T., Nakagawa T., Shimada N., and Kobayashi K. J. Antibiot. 47 (1994) 697
13. Stierle D.B., Stierle A.A., and Ganser B. J. Nat. Prod. 60 (1997) 1207-1209
14. Ali A., Mackeen M.M., Hamid M., Aun Q.B., Zauyah Y., Azimahtol H.L.P., and Kawazu K. Planta Med. 63 (1997) 81-83
15. Falomir E., Murga J., Cardaa M., and Marcob J.A. Tetrahedron Lett. 44 (2003) 539-541
16. Chenevert R., Courchesne G., and Caron D. Tetrahedron: Asymmetry 14 (2003) 2567-2571
17. Achenbach H., and Wittman G. Tetrahedron Lett. 37 (1970) 3259-3262
18. Pepping J.J. Health Syst. Pharmacol. 56 (1999) 957-958
19. Dharmaratne H.R., Nanayakkara N.P., and Khan A. Phytochemistry 59 (2002) 429-433
20. Bilia A.R., Gallon S., and Vincieri F.F. Life Sci. 70 (2002) 2581-2597
21. Singh Y.N., and Singh N.N. CNS Drugs 16 (2002) 731-743
22. Pittler M.H., and Ernst E. J. Clin. Psychopharmacol. 20 (2000) 84-89
23. Achenbach H., and Huth H. Tetrahedron Lett. 15 (1974) 119-120
24. For a racemic synthesis see:. Friesen R.W., and Vanderwal C. J. Org. Chem. 61 (1996) 9103-9110
25. For asymmetric synthesis of (+)-dihydrokawain-5-ol see:. Arai Y., Masuda T., Yoneda S., Masaki Y., and Shiro M. J. Org. Chem. 65 (2000) 258-262
26. Singh R.P., and Singh V.K. J. Org. Chem. 69 (2004) 3425-3430
27. Kamal A., Krishnaji T., and Reddy P.V. Tetrahedron: Asymmetry 18 (2007) 1775-1779
28. Kamal A., Reddy P.V., and Prabhakar S. Tetrahedron: Asymmetry 20 (2009) 1120-1124
29. Kamal A., Krishnaji T., and Reddy P.V. Tetrahedron: Asymmetry 18 (2007) 1775-1779
30. Kamal A., Krishnaji T., and Reddy P.V. Tetrahedron Lett. 48 (2007) 7232-7235
31. Kamal A., Krishnaji T., and Khanna G.B.R. Tetrahedron Lett. 47 (2006) 8657-8660
32. Evans D.A., and Starr J.T. J. Am. Chem. Soc. 125 (1981) 13531-13540
33. Evans D.A., and Dow R.L. Tetrahedron Lett. 27 (1986) 1007-1010
34. Evans D.A., and Sjogren E.B. Tetrahedron Lett. 27 (1986) 3119-3122
35. Mapp A.K., and Heathcock C.H. J. Org. Chem. 64 (1999) 23-27
36. Yokoe H., Sasaki H., Yoshimura T., Shindo M., Yoshida M., and Shishido K. Org. Lett. 4 (2007) 969-971
37. Evans D.A., Welch D.S., Speed A.W.H., Moniz G.A., and Reichelt A. J. Am. Chem. Soc. 131 (2009) 3840-3841
38. Ho G.-J., and Mathre D.J. J. Org. Chem. 60 (1995) 2271-2273
39. Evans D.A., Bartroli J.A., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127-2129
40. Evans D.A., and Bender S.L. Tetrahedron Lett. 27 (1986) 799-802
41. Jones T.K., Reamer R.A., Desmond R., and Miles S.G. J. Am. Chem. Soc. 112 (1990) 2998
42. Hulme A.N., and Rosser E.M. Org. Lett. 9 (2002) 265-267
43. Sharma G.V.M., and Cherukupalli G.R. Tetrahedron Asymmetry 17 (2006) 1081-1088
44. Crouch R.D. Tetrahedron 60 (2004) 5833-5871 and references cited therein
45. Hori H., Nishida Y., Ohrui H., and Meguro H. J. Org. Chem. 54 (1989) 1346-1353