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RESEARCH ARTICLE

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A First Generation Chemoenzymatic Synthesis of (+)-Galanthamine

Martin G. Banwell ^A ^B , Xinghua Ma ^A , Ochitha P. Karunaratne ^A and Anthony C. Willis ^A

+ Author Affiliations

- Author Affiliations

^A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.

^B Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 63(10) 1437-1447 https://doi.org/10.1071/CH10201
Submitted: 17 May 2010 Accepted: 6 July 2010 Published: 1 October 2010

Abstract

A total synthesis of (+)-galanthamine [(+)-1] has been achieved using the readily available and enantiomerically pure metabolite 2 as starting material. The quaternary carbon centre (C8a) associated with target 1 was constructed using the Eschenmoser–Claisen rearrangement reaction.

Acknowledgements

The authors thank the Institute of Advanced Studies, The Australian National University, and the Australian Research Council for generous financial support as well as Dr Hank Fales (National Institutes of Health, Maryland, USA) for an authentic sample of (–)-galanthamine.

References

[1] For a review detailing the isolation and development of (–)-galanthamine as a drug see: Heinrich M., Teoh H. L., J. Ethnopharmacol. 2004, 92, 147. doi:10.1016/J.JEP.2004.02.012

[2] For a review dealing with the synthesis and pharmacology of (–)-galanthamine see: Marco-Contelles J., do Carmo Carreiras M., Rodríguez C., Villarroya M., García A. G., Chem. Rev. 2006, 106, 116. doi:10.1021/CR040415T

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