Precursors for the Oxidative Tandem Cyclization ofDiphenols to Galanthamine Analogs
FULL TEXT PDF (ENGLISH)

Keywords

Tandem cyclization, isopropyl-ether protecting group, O-dealkylation,deoxygenation of benzyl alcohols.

How to Cite

[1]
Matthias Treu and Ulrich Jordis trans. 2024. Precursors for the Oxidative Tandem Cyclization ofDiphenols to Galanthamine Analogs. Food Additives and Contaminants. 41, 1 (Jun. 2024), 18–25. DOI:https://doi.org/10.5281/yxt85e21.

Abstract

Methods for the preparation of 4-bromo-5-[2-(4-hydroxybenzyl)benzyl]-2-methoxyphenol and 4-bromo-5-[4-(4-hydroxyphenyl)butyl]-2-methoxyphenol are described.

FULL TEXT PDF (ENGLISH)

References

Giacobini, E. Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to futureapplications.Neurochem. Int.1998,32, 413 - 419.

Arisawa, M.; Tohma, H.; Kita, Y. Development of intramolecular oxidative phenolic couplingreactions using hypervalent iodine (III) reagents and their application to the synthesis of

Amaryllidaceae alkaloids.Yakugaki Zasshi, J. Pharm. Soc. Japan2000,120, 1061 - 1073.

Franck, B.; Dunkelmann, G.; Lubs, H. J. Alkaloid syntheses by oxidative condensation underbiogenetic conditions. IX. Synthesis of a morphinan derivative by oxidative ring closure.Angew.Chem., Int. Ed. Engl.1967,6, 1075 - 1076.

Schwartz, M. A.; Holton, R. A. Intramolecular oxidative phenol coupling. II. Biogenetic-typesynthesis of (±)-maritidine.J. Amer. Chem. Soc.1970,92, 1090 - 1092.

Kametani, T.; Yamaki, K.; Yagi, H.; Fukumoto, K. Studies on the syntheses of heterocycliccompounds. CCCXV. Modified total synthesis of (-)-galanthamine through phenol oxidation.J.Chem. Soc. C1969, 2602 – 2605.

Barton, D. H. R.; Kirby, G. W. Phenol oxidation and biosynthesis. V. Synthesis of galanthamine.

Chem. Soc.1962, 806 - 817.

Kametani, T.; Seino, C.; Yamaki, K.; Shibuya, S.; Fukumoto, K.; Kigasawa, K.; Satoh, F.; Hiiragi,M.; Hayasaka, T. Syntheses of heterocyclic compounds. CCCLXXXVI. Alternative total syntheses

of galanthamine and N-benzylgalanthamine iodide. J. Chem. Soc. C1971, 1043 - 1047.

(a) 1,3-Dihydrospiro(isobenzofuran)ene. NL 7416115,1975[Chem. Abstr.: 84:164641]. (b)Heidenreich, J. Ueber Indoxazene.Chem. Ber.1894,27, 1452 - 1456.

Munakata, K.; Tanaka, S.; Toyoshima, S. Therapy for urolithiasis with hydroxamic acids. I.Synthesis of new N-(aroyl)glycinohydroxamic acid derivatives and related compounds.Chem.Pharm. Bull.1980,28, 2045 – 2051.

Martin, L. L.; Klioze, S. S.; Worm, M.; Crichlow, C. A.; Geyer, H. M.,III; Kruse, H. Synthesis ofspiro[isobenzofuran-1(3H),4'-piperidines]

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.

Copyright (c) 2024 Food Additives and Contaminants