Stereocontrolled synthesis of the aconitine D ring from -glucose

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. All five oxygen substituents and all six skeletal carbon a...

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Published in:Organic & biomolecular chemistry 2024-05, Vol.22 (21), p.4347-4352
Main Authors: Pocock, Ian A, Doulcet, Julien, Rice, Craig R, Sweeney, Joseph B, Gill, Duncan M
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Summary: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. 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00561a