Short asymmetric syntheses of bioactive β-aryl ethanolamine derivatives via the highly diastereoselective delta lactol oxy-Michael addition

Tetrahedron Asymmetry

Volumn 15, Issue 2, 2004, Pages 195-197

  Buchanan, David J ^a   Dixon, Darren J ^a   Scott, Mark S ^a   Lainé, Dramane I ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AEGELINE; ALKENE DERIVATIVE; ANION; ETHANOLAMINE DERIVATIVE; NITRO DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PRONETALOL; TEMBAMIDE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DRUG ACTIVITY; DRUG SYNTHESIS; MICHAEL ADDITION; POLYMERIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY; TECHNIQUE;

EID: 0346339572     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.018     Document Type: Article

References (37)

1. Hieble J.P., Bondinell W.E., Ruffolo R.R. J. Med. Chem. 38:1995;3415.
2. Ruffolo R.R., Bondinell W., Hieble J.P. J. Med. Chem. 38:1995;3681.
3. Main B.G., Tucker H. Roberts S.M., Price B.S. Medicinal Chemistry: The Role of Organic Chemistry in Drug Design. 1985;Academic Press, London. Chapter 5.
4. Lunts L.H.C. Roberts S.M., Price B.S. Medicinal Chemistry: The Role of Organic Chemistry in Drug Design. 1985;Academic Press, London. Chapter 4.
5. Almirante L., Murmann W. J. Med. Chem. 9:1966;650.
6. Howe R., Crowther A.F., Stephenson J.S., Rao B.S., Smith L.H. J. Med. Chem. 11:1968;1000.
7. Millership J.S., Fitzpatrick A. Chirality. 5:1993;573. and references cited therein.
8. Ruffolo R.R. Tetrahedron. 47:1991;9953.
9. Howe R., Rao B.S. J. Med. Chem. 11:1968;1118.
10. Enders D., Haertwig A., Raabe G., Runsink J. Angew. Chem., Int. Ed. Engl. 35:1996;2388-2390.
11. Enders D., Haertwig A., Raabe G., Runsink J. Eur. J. Org. Chem. 1998;1771-1792.
12. Enders D., Haertwig A., Runsink J. Eur. J. Org. Chem. 1998;1793-1801.
13. Adderley N.A., Buchanan D.J., Dixon D.J., Lainé D.I. Angew. Chem., Int. Ed. Engl. 35:2003;4241.
14. For amino alcohol synthesis via the Henry reaction, see: Sasai H., Itoh N., Suzuki T., Shibasaki M. Tetrahedron Lett. 34:1993;855.
15. Sasai H., Suzuki T., Itoh N., Arai S., Shibasaki M. Tetrahedron Lett. 34:1993;2657.
16. Chinchilla R., Nájera C., Sanchez-Agulló P. Tetrahedron: Asymmetry. 5:1994;1393.
17. Shibasaki M., Sasai H., Arai T. Angew. Chem. 109:1997;1290.
18. Angew. Chem., Int. Ed. Engl. 36:1997;1236.
19. Sasai H., Tokunaga T., Watanabe S., Suzuki T., Itoh N., Shibasaki M. J. Org. Chem. 60:1995;7388.
20. Trost B.M., Yeh V.S.C., Ito H., Bremeyer N. Org. Lett. 4:2002;2621.
21. For other synthetic routes to amino alcohols see, for example: Klunder J.M., Ko S.Y., Sharpless K.B. J. Org. Chem. 51:1986;3710.
22. For previous total syntheses, see: Yadav J.S., Reddy P.T., Nanda S., Rao A.B. Tetrahedron: Asymmetry. 12:2001;3381.
23. Cho B.T., Kang S.K., Shin S.H. Tetrahedron: Asymmetry. 13:2002;1209.
24. Brown R.F.C., Jackson W.R., McCarthy T.D. Tetrahedron: Asymmetry. 4:1993;205.
25. Brown R.F.C., Donohue A.C., Jackson W.R., McCarthy T.D. Tetrahedron. 50:1994;13739.
26. For previous total syntheses, see: Solladié-Cavallo A., Diep-Vohuule A. J. Org. Chem. 60:1995;3494.
27. Jackson W.R., Jacobs H.A., Jayatilake G.S., Matthews B.R., Watson K.G. Aust. J. Chem. 43:1990;2045. and references cited therein.
28. Kuck A.M., Albonico S.M., Deulofeu V. Chem. Ind. 1966;945.
29. Chatterjee A., Bose S. J. Indian Chem. Soc. 29:1952;425.
30. Johns S.R., Lamberton J.A., Price J.R. Aust. J. Chem. 20:1967;2795.
31. Johns S.R., Lamberton J.A., Tweeddale H.J., Willing R.I. Aust. J. Chem. 22:1969;2233.
32. Somoanathan R., Aguilar H.R., Ventura R., Smith K.M. Synth. Commun. 13:1983;273.
33. Shoeb A., Kapil R.S., Popli S.P. Phytochemistry. 12:1973;2071.
34. Feng H., Yunxin B., Altom J.D., Corey E.J. J. Am. Chem. Soc. 121:1999;6771.
35. Available in two steps from enantiopure (S)-propylene oxide, see: Dixon D.J., Ley S.V., Tate E.W. J. Chem. Soc., Perkin Trans. 1. 2000;2385.
36. 1H NMR (500 MHz) spectrum of the crude reaction mixture.
37. MP-TsOH, available from Argonaut Technologies.