Stereocontrolled synthesis of the aconitine D ring from D-glucose

Ian A Pocock; Julien Doulcet; Craig R Rice; Joseph B Sweeney; Duncan M Gill

doi:10.1039/d4ob00561a

Stereocontrolled synthesis of the aconitine D ring from D-glucose

Org Biomol Chem. 2024 May 10. doi: 10.1039/d4ob00561a. Online ahead of print.

Authors

Ian A Pocock¹, Julien Doulcet^{1

2}, Craig R Rice¹, Joseph B Sweeney^{1

3}, Duncan M Gill^{1

4}

Affiliations

¹ Department of Chemical Sciences, University of Huddersfield, Huddersfield, HD1 3DH, UK. d.m.gill@hud.ac.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.

PMID: 38726909
DOI: 10.1039/d4ob00561a

Abstract

The synthesis of a fully oxygenated aconitine D ring precursor from (D)-(+)-glucose is described. The route features a highly diastereoselective alkynyl Grignard ketone addition and a base-mediated enelactone to 1,3-diketone rearrangement.