A Convergent Synthesis of the Cardenolide Skeleton: Intramolecular Aldol Condensation via Reduction of α-Bromoketones
- 27 June 2002
- journal 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
This publication has 17 references indexed in Scilit:
- Synthesis of Tropane Alkaloids via Enantioselective Deprotonation of TropinoneThe Journal of Organic Chemistry, 1995
- Stereocontrolled synthesis of optically active 14β-hydroxy steroids and other steroid derivativesCanadian Journal of Chemistry, 1992
- Stereoselective synthesis of cis-decalins via Diels–Alder and double Michael addition of substituted Nazarov reagentsCanadian Journal of Chemistry, 1992
- Generalization, Alteration, and Enhancement of the Stereoselectivity in the Cieplak-Mode Reductions of 4-Alkoxy(or Silyloxy)cyclohexanonesChemistry Letters, 1990
- Lanthanides in organic synthesis. 8. 1.3-Asymmetric induction in intramolecular Reformatskii-type reactions promoted by samarium diiodideJournal of the American Chemical Society, 1987
- Direct, regiospecific 2-lithiation of pyridines and pyridine 1-oxides with in situ electrophilic trappingThe Journal of Organic Chemistry, 1983
- A simple method for the efficient synthesis of unsaturated .beta.-dicarbonyl compoundsThe Journal of Organic Chemistry, 1981
- Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agentsJournal of the American Chemical Society, 1980
- A Convenient Synthesis OF 2-CarbomethoxycyclohexanoneSynthetic Communications, 1976
- Synthese von α‐halogenierten, α.β‐ungesättigten Carbonsäuren mit Triphenylphosphin‐halogen‐carbomethoxy‐methylenenEuropean Journal of Inorganic Chemistry, 1961