Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalysed acylations

Tetrahedron Asymmetry

Volumn 14, Issue 5, 2003, Pages 567-576

  Hull, Jonathan D ^a   Scheinmann, Feodor ^a   Turner, Nicholas J ^b  

^a Ultrafine UFC Ltd   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BUFURALOL; LEVACETYLMETHADOL; METHADONE; PROPANOL; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CONTROLLED STUDY; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 0037424362     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00019-3     Document Type: Article

References (27)

1. Grant, K. Scotland on Sunday, 26th August, 2001, p. 13.
2. Morley J.S., Makin M.K. Pain Rev. 5:1998;51.
3. Casy A.F., Parfitt R.T. Opioid Analgesics. 1986;303 Plenum Press, New York.
4. (a) Wolff K., Rostami-Hodjegan A., Shires S., Hay A.W.M., Freely M., Calvert R., Raistrick D., Tucker G.T. Brit. J. Pharmacol. 44:1997;325. and references cited therein;
5. (b) Drugs Misuse and Dependence, Department of Health (UK), 1999, p. 104.
6. th Edition, Merck & Co., Inc., NJ., 1996, p. 1015, monograph no. 6008.
7. Brode W.R., Hill M.W. J. Org. Chem. 13:1948;191.
8. Larsen A.A., Tullar B.F., Elpern B., Buck J.S. J. Am. Chem. Soc. 70:1948;4194.
9. Howe E.E., Sletzinger M. J. Am. Chem. Soc. 71:1949;2935.
10. Walton E., Ofner P., Thorp R.H. J. Chem. Soc. 1949, 648;
11. Adams, D. unpublished work.
12. Barnett C.J., Smirz J.C. J. Org. Chem. 1976;710.
13. Fluka Laboratory Chemicals, 2001/2002, p. 643, catalogue no. 77637 and 69769.
14. Fluka Laboratory Chemicals, 2001/2002, p. 509, catalogue no. 39300.
15. Fothergill, G. A.; Osbond, J. M.; Wickins, J. C. Arneim.-Forsch. 1977, 27, 978; ibid, Experientia 1975, 31, 1322.
16. Fothergill, G. A.; Osbond, J. M.; Wickins, J. C. Arneim.-Forsch. 1977, 27, 978; ibid, Experientia 1975, 31, 1322.
17. Machin P.J., Hurst D.N., Osbond J.M. J. Med. Chem. 28:1985;1648.
18. Goering H., Eikenberry H., Koermer G., Lattimer C. J. Am. Chem. Soc. 96:1974;1493.
19. Poupaert, J. H.; Van der Jeugd, P.; Gerardy, B. M.; Claesen, M.; Dumont, P. J. Chem. Res. (S) 1981, 192; J. Chem. Res. (M) 1981, 2484.
20. Poupaert, J. H.; Van der Jeugd, P.; Gerardy, B. M.; Claesen, M.; Dumont, P. J. Chem. Res. (S) 1981, 192; J. Chem. Res. (M) 1981, 2484.
21. Bockmuehl V.M., Ehrhart G. Liebigs Ann. 561:1949;52.
22. LAAM in the Treatment of Opiate Addiction, Chapter 1, The National Clearing House for Alcohol and Drug Information, http://www.health.org/govpubs/bkd170/22c.htm .
23. European Agency for the Evaluation of Medicinal Products, 19th April 2001, EMEA/8776/01, http://www.emea.eu.int/ .
24. May, E. L.; Mosettig, E. J. Org. Chem. 1948, 13, 459 and 663.
25. Pohland A., Marshall F.J., Carney T.P. J. Am. Chem. Soc. 71:1949;460.
26. Collier P., Scheinmann F., Stachulski A.V. J. Chem. Res. (S). 1994;312.
27. Ref. 4, p. 934, monograph no. 5492.