Construction of the tricyclic A-B-C core of the Veratrum alkaloids.

Organocatalyzed enantioselective allylation of 2-iodocyclohexenone followed by methylation and oxy-Cope rearrangement delivered enantiomerically enriched 2-methyl 3-allyl cyclohexanone, which engaged in acid-catalyzed Robinson annulation to give the bicyclic enone. Subsequent elaboration of the pendant allyl group into an α-diazo β-keto ester set the stage for Rh-mediated cyclization to deliver the tricyclic A-B-C core of the Veratrum alkaloids.

Citation

Douglass F Taber, James F Berry. Construction of the tricyclic A-B-C core of the Veratrum alkaloids. The Journal of organic chemistry. 2013 Sep 06;78(17):8437-41

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PMID: 23859604

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