ArticleJournal of the American Chemical Society2016
Concise Enantioselective Total Synthesis of Cardiotonic Steroids 19-Hydroxysarmentogenin and Trewianin Aglycone.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Bioinspired Synthesis of Twin abeo-Steroids Bufogargarizins A and B via a Divergent Intramolecular Aldol Addition Reaction.Angewandte Chemie (International ed. in English) · 2026Article
- Development of CPA-Catalyzed β-Selective Reductive Amination of Cardenolides for the Synthesis and Biological Evaluation of Hydrolytically Stable Analogs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Chemoenzymatic synthesis of the cardenolide rhodexin A and its aglycone sarmentogenin.Beilstein journal of organic chemistry · 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
- Article
- Lipidomics combined with transcriptomic and mass spectrometry imaging analysis of the Asiatic toad (Bufo gargarizans) during metamorphosis and bufadienolide accumulation.Chinese medicine · 2022Article
- Progress toward the De Novo Asymmetric Synthesis of Euphanes.Organic letters · 2022Article
- Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B.The Journal of organic chemistry · 2021Article
- From anOrganic letters · 2021Article
- Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.European journal of organic chemistry · 2020Article
- A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids.Nature communications · 2019Article
- A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ.Nature communications · 2019Article
- 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
- 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
- Synthetic nat- or ent-steroids in as few as five chemical steps from epichlorohydrin.Nature chemistry · 2018Article
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Authors and funding
3 authors.
Funding
Abstract
The expedient and scalable approach to cardiotonic steroids carrying oxygenation at the C11- and C19-positions has been developed and applied to the total asymmetric synthesis of steroids 19-hydroxysarmentogenin and trewianin aglycone as well as to the assembly of the panogenin core. This new approach features enantioselective organocatalytic oxidation of an aldehyde, diastereoselective Cu(OTf)2-catalyzed Michael reaction/tandem aldol cyclizations, and one-pot reduction/transposition reactions allowing a rapid (7 linear steps) assembly of a functionalized cardenolide skeleton. The ability to quickly set this steroidal core with preinstalled functional handles and diversity elements eliminates the need for difficult downstream functionalizations and substantially improves the accessibility to the entire class of cardenolides and their derivatives for biological evaluation.
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