Stereocontrolled synthesis of the aconitine D ring from d-glucose

Author:

Pocock Ian A.1ORCID,Doulcet Julien12,Rice Craig R.1ORCID,Sweeney Joseph B.13,Gill Duncan M.14ORCID

Affiliation:

1. Department of Chemical Sciences, University of Huddersfield, Huddersfield, HD1 3DH, UK

2. Department of Chemistry, University of Lancaster, Lancaster, LA1 4YB, UK

3. Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK

4. Department of Pharmacy, University of Huddersfield, Huddersfield, HD1 3DH, UK

Abstract

All five oxygen substituents and all six skeletal carbon atoms of the aconitine D ring are derived from d-glucose in a fully stereocontrolled synthesis featuring an enelactone to diketone rearrangement.

Funder

Leverhulme Trust

University of Huddersfield

Publisher

Royal Society of Chemistry (RSC)

Reference45 articles.

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2. Diterpenoid alkaloids

3. The effects of Aconitum alkaloids on the central nervous system

4. M. H.Benn and J. M.Jacyno , in Alkaloids Chemical & Biological Perspectives , ed. S. W. Pelletier , J. Wiley & Sons, Inc. , New York , 1983 , vol. 1 , pp. 153–220

5. P.Ovidius Naso , Metamorphoses, I, 147, Penguin Classics , London , 2004

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