New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2087-2088

  Czollner, Laszlo ^a   Frantsits, Werner ^a   Küenburg, Bernhard ^a   Hedenig, Ursula ^b   Fröhlich, Johannes ^b   Jordis, Ulrich ^b  

^a Sanochemia AG   (Austria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Asymmetric synthesis; Phenols; Polycyclic heterocyclic compounds

Indexed keywords

GALANTAMINE;

ALZHEIMER DISEASE; ARTICLE; CHIRALITY; DRUG SYNTHESIS; DRUG TRANSFORMATION; REDUCTION;

EID: 0032499149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00294-9     Document Type: Article

References (11)

1. [1] Review: Bores GM Kosley Jr. RW Drugs Future, 1996, 21, 621-635.
2. [2] For small-scale syntheses of galanthamine see: a) Barton DHR, Kirby GW. J. Chem. Soc. 1962, 806.
3. b) Kametani T, Yamaki T, Yagi H, Fukumoto K. J. Chem. Soc. 1969, 2602.
4. c) Szewczyk J, Lewin A, Caroll FI, J. Het. Chem. 1988, 25, 1809-1811.
5. d) Shieh WC, Carlson JA. J. Org. Chem. 1994, 59, 5463.
6. e) Czollner L; Fröhlich J; Jordis U, Küenburg B. AT 401058 (Waldheim), Chem. Abstr. 125:196086.
7. f) references cited by Chaplin [5].
8. 4 will be reported elsewhere.
9. [4] The details of this chiral transformation, including the determination of the optical purity of 1 and 5 by chiral capillary electrophoresis (CE) and their x-ray crystallography, will be reported elsewhere.
10. [5] For a recent reference on the synthesis of narwedine see: Chaplin DA; Fraser N, Tiffin PD. Tetrahedron Lett. 1997, 38, 79311 .
11. 4) / MeOH 92.5:7.5 at 1.2 mL/min (isocratic) and UV detection at 285 nm.