Total synthesis of galanthamine, analogues and derivatives...

Details Total synthesis of galanthamine, analogues and derivatives... Total synthesis of galanthamine, analogues and derivatives...

2002-06-14

2010-06-01

Kifle, Bruck (Department: 1624)

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

Organic compounds

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

C546S065000, C546S110000, C549S265000, C549S342000, C549S358000, C549S399000, C549S446000, C549S458000

Reissue Patent

active

RE041366

ABSTRACT:
The invention relates to a method for the synthesis of galanthamine, the derivatives and analogues thereof of formula (1) where R1=a hydrogen atom, R2=a hydroxy group, R1and R2together form ═O, R3, R4, and R5independently=a hydrogen atom, a hydroxy group or a (C1-C2)alkoxy group, R6═H, (C1-C12)alkyl, (CH2)nNR7R8, or —(CH2)nN+R7R8R9where n=1 to 12, Z=two hydrogen atoms, or an oxygen atom and X=an oxygen, sulphur or nitrogen atom, or a —SO, —SO2, or —NR6group where R6is as defined above or is an amine protecting group.

REFERENCES:
A. L. Harvey, “The Pharmacology of Galanthamine and its Analogues”, Pharmac. Ther. vol. 68, No. 1, pp. 113-128, 1995.
Weinstock, “Selectivity of Cholinesterase Inhibition, Clinical Implications for the Treatment of Alzheimer's Disease”, CNS Drugs Oct. 12, 1999 (4), pp. 307-323.
Barton et al., “Phenol Oxidation and Biosynthesis. Part V. The Synthesis of Galanthamine”, J. Chem. Soc. (1962), pp. 806-817.
Czollner et al., “New Kilogram-Synthesis of the Anti-Alzheimer Drug (−)-Galathamine”, Tetrahedron Letters 39 (1998), pp. 2087-2088.
Krikorian et al., “New Achievements in the Field of Intramolecular Phenolic Coupling Reactions, Using Hypervalent (III) Iodine Reagent: Synthesis of Galanthamine”, Synthetic Communications, 30(16), 2833-2846 (2000), pp. 2833-2846.
Ishizaki et al., “Synthetic Approaches toward Spiro[2,3-dihydro-4H-1-benzopyran-4,1′-cyclohexan]-2-one Derivatives via Radical Reactions: Total Synthesis of (±)-Lycoramine”, J. Org. Chem. 1993, 58, 3877-3885.
Gras et al., “A formal sythesis of (±O lycoramine via an intramolecular Heck reaction”, Tetrahedron Letters 40 (1999), pp. 9243-2944.
Trost et al., “Enantioselective Total Synthesis of (−)-Galanthamine”, J. Am. Chem. Soc. 2000, 122, pp. 11262-11263.
Pilger et al., “A New Stereoselective Approach Towards the Galanthamine Ring System via an Intramolecular Heck Reaction”, Synlett 2000, No. 8, pp. 1163-1165.
Parsons et al., “A general approach to the galanthamine ring system”, Tetrahedron Letters 42 (2001), pp. 2209-2211.
T. G. Back, “Dehydrogenation of Hydrazines and of 4-Azacholestan-3-one with Benzenseleninic Acid and Benzeneseleninic Anhydride”, J.C.S. Chem. Comm., 1978 (pp. 278-279).
Barton et al., “Dehydrogenation of Steroidal and Triterpenoid Ketones using Benzene-seleninic Anhydride”, J.C.S.Perkin I (1980), pp. 2209-2212.
Barton et al., “Dehydrogenation of Lactones using Benzeneseleninic Anhydride”, J. Chem. Soc. Perkin Trans. I, 1982, pp. 1919-1922.
Barton et al., “A Practical Catalytic Method for the Preparation of Steroidal 1,4-Dien-3-ones by Oxygen Atom Transfer from Iodoxybenzene to Diphenyl Di-selende”, J. Chem. Soc. Perkin Trans. I, 1982, pp. 1947-1952).

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