A Convergent Synthesis of the Cardenolide Skeleton: Intramolecular Aldol Condensation via Reduction of α-Bromoketones
- 27 June 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (16) , 5669-5672
- https://doi.org/10.1021/jo025612b
Abstract
Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and γ,δ-unsaturated β-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis.Keywords
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