ArticleOrganic letters2018
Enantioselective Total Synthesis of Cannogenol-3-O-α-l-rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.
Article in Organic letters, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 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
- Total Synthesis of Cardenolides Acospectoside A and Acovenoside B.Molecules (Basel, Switzerland) · 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
- The mechanistic role of cardiac glycosides in DNA damage response and repair signaling.Cellular and molecular life sciences : CMLS · 2023Review
- Development of α-Selective Glycosylation with l-Oleandral and Its Application to the Total Synthesis of Oleandrin.Organic letters · 2023Article
- 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
- 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
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2 authors.
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Abstract
A concise and scalable enantioselective total synthesis of the natural cardenolides cannogenol and cannogenol-3-O-α-l-rhamnoside has been achieved in 18 linear steps. The synthesis features a Cu(II)-catalyzed enantioselective and diastereoselective Michael reaction/tandem aldol cyclization and a one-pot reduction/transposition, which resulted in a rapid (6 linear steps) assembly of a functionalized intermediate containing C19 oxygenation that could be elaborated to cardenolide cannogenol. In addition, a strategy for achieving regio- and stereoselective glycosylation at the C3 position of synthetic cannogenol was developed and applied to the preparation of cannogenol-3-O-α-l-rhamnoside.
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