ArticleJournal of the American Chemical Society2015
Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Densely-functionalized bicyclic cyclopentanones by combined photoinduced 6-Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Bioinspired Synthesis of Twin abeo-Steroids Bufogargarizins A and B via a Divergent Intramolecular Aldol Addition Reaction.Angewandte Chemie (International ed. in English) · 2026Article
- Bismuth Meets Olefins: Ethylene Activation and Reversible Alkene Insertion into Bi─N Bonds.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of Bufadienolide Cinobufagin via Late-Stage Singlet Oxygen Oxidation/Rearrangement Approach.Organic letters · 2024Article
- Selective (α)-l-Rhamnosylation and Neuroprotective Activity Exploration of Cardiotonic Steroids.ACS medicinal chemistry letters · 2024Article
- Mechanistic elucidation of the tandem Diels-Alder/(3 + 2) cycloadditions in the design and syntheses of heterosteroids.Journal of molecular modeling · 2022Article
- Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B.The Journal of organic chemistry · 2021Article
- Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.Chemical reviews · 2021Article
- Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.European journal of organic chemistry · 2020Article
- Regioselective single pot C3-glycosylation of strophanthidol using methylboronic acid as a transient protecting group.The Journal of antibiotics · 2019Article
- Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.Journal of the American Chemical Society · 2019Article
- Transient [3,3] Cope rearrangement of 3,3-dicyano-1,5-dienes: computational analysis and 2-step synthesis of arylcycloheptanes.Chemical science · 2018Article
- Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C.RSC advances · 2018Article
- Copper(II)-Catalyzed Tandem Decarboxylative Michael/Aldol Reactions Leading to the Formation of Functionalized Cyclohexenones.Organic letters · 2018Article
- Enantioselective Total Synthesis of Cannogenol-3-O-α-l-rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.Organic letters · 2018Article
- Concise Enantioselective Total Synthesis of Cardiotonic Steroids 19-Hydroxysarmentogenin and Trewianin Aglycone.Journal of the American Chemical Society · 2016Article
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6 authors.
Funding
Abstract
A new scalable enantioselective approach to functionalized oxygenated steroids is described. This strategy is based on chiral bis(oxazoline) copper(II) complex-catalyzed enantioselective and diastereoselective Michael reactions of cyclic ketoesters and enones to install vicinal quaternary and tertiary stereocenters. In addition, the utility of copper(II) salts as highly active catalysts for the Michael reactions of traditionally unreactive β,β'-enones and substituted β,β'-ketoesters that results in unprecedented Michael adducts containing vicinal all-carbon quaternary centers is also demonstrated. The Michael adducts subsequently undergo base-promoted diastereoselective aldol cascade reactions resulting in the natural or unnatural steroid skeletons. The experimental and computational studies suggest that the torsional strain effects arising from the presence of the Δ(5)-unsaturation are key controlling elements for the formation of the natural cardenolide scaffold. The described method enables expedient generation of polycyclic molecules including modified steroidal scaffolds as well as challenging-to-synthesize Hajos-Parrish and Wieland-Miescher ketones.
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