A Convergent Synthesis of the Cardenolide Skeleton: Intramolecular Aldol Condensation via Reduction of α-Bromoketones
The Journal of Organic Chemistry2002Vol. 67(16), pp. 5669–5672
Citations Over TimeTop 12% of 2002 papers
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 gamma,delta-unsaturated beta-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.
Related Papers
- → Recent Advancement and Novel Application of Organocatalyzed AldolCondensation Reactions: A Comprehensive Review(2022)7 cited
- → Stereoselective aldol condensations via alkenyloxy dialkoxyboranes: synthetic applications using thioesters(1984)42 cited
- → Remarkable long range effects on the diastereoface selectivity in an aldol condensation(1999)16 cited
- → Aldol Reaction and Aldol Condensation(2010)
- → Asymmetric aldol reactions(1996)