Method of manufacture of (-)-galanthamine in high yield and puri

Details Method of manufacture of (-)-galanthamine in high yield and puri Method of manufacture of (-)-galanthamine in high yield and puri

1994-04-08

1995-06-27

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D49108

Patent

active

054281598

ABSTRACT:
(-)-Galanthamine is obtained in substantially high yield and purity substantially without concomitant production of epigalanthamine by conversion of racemic narwedine to (-)-narwedine and subsequent reduction to (-)-galanthamine using bulky organo-aluminum or organo-boron reducing agents.

REFERENCES:
Barton et al, J. Chem. Soc. 1962, 806-817. "Phenol Oxidation and Biosynthesis. Part V. The Synthesis of Galanthamine".
Shimizu et al, Heterocycles 1977, 8, 277-282. "A Biogenetic-Type Asymmetric Synthesis of Optically Active Amaryllidaceae Alkaloids . . . ".
Shimizu et al, Chem. Pharm. Bull. 1978, 26, 3765-3771. "Stereochemical Studies. LIV. A Biogenetic-Type Asymmetric Synthesis of Optically Active Galanthamine from L-Tyrosine".
Szewczyk et al, J. Heterocycl. Chem 1988, 25, 1809-1811 "An Improved Synthesis of Galanthamine".
Kametani et al, J. Org. Chem. 1971, 36, 1295-1297 "Studies on the Synthesis of Heterocyclic Compounds. CCCXCVI. An Alternative Total Synthesis of (.+-.)-Galanthamine."
Kametani et al, J. Chem. Soc. Perkin Trans. 1, 1972, 1513 "Studies on the Synthesis of Heterocyclic Compounds. Part CDLXVI. Synthesis of Narwedine Type Enones By Photochemical Cyclisation."
Kametani et al, J. Heterocycl. Chem. 1973, 10, 35 "Studies on the Synthesis of Heterocyclic Compounds. Part DVII(1) A Synthesis of (.+-.)-N-Norgalanthamine."
Vlahov et al, Tetrahedron 1989, 45, 3329 "Synthesis of Galanthamine and Related Alkaloids--New Approaches. I.".
Holton et al, J. Am. Chem. Soc. 1988, 110, 314-316 "Palladium-Mediated Biomimetic Synthesis of Narwedine".

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