ArticleThe Journal of antibiotics2019
Regioselective single pot C3-glycosylation of strophanthidol using methylboronic acid as a transient protecting group.
Article in The Journal of antibiotics, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
8 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
- 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
- Development of Recyclable Polystyrene-Supported Phosphonic Acid Resins for Carbohydrate Immobilization and Glycosylation.The Journal of organic chemistry · 2023Article
- 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
- Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.European journal of organic chemistry · 2020Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
This manuscript describes a single pot protocol for the selective introduction of unprotected sugars to the C3 position of the cardiotonic steroid strophanthidol. These reactions proceed with high levels of regiocontrol (>20:1 rr) in the presence of three other hydroxyl functionalities including the C19 primary hydroxyl group and could be applied to different sugars to provide the deprotected cardiac glycosides upon work up (5 examples, 77-69% yield per single operation). The selective glycosylation of the less reactive C3 position is accomplished by the use of traceless protection with methylboronic acid that blocks the C5 and C19 hydroxyls by forming a cyclic boronic ester, followed by in situ glycosylation and a work up with ammonia in methanol to remove the boronic ester and the carbohydrate ester protecting groups.
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Registered trials
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