ArticleJournal of the American Chemical Society2017
Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 43 citations in OpenAlex.
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- Synthesis and immunochemical studies of linear oligoglucosides structurally related to the cyclic β-(1→2)-D-glucan of Brucella.Communications chemistry · 2025Article
- Lithium Enolate with a Lithium-Alkyne Interaction in the Enantioselective Construction of Quaternary Carbon Centers: Concise Synthesis of (+)-Goniomitine.Angewandte Chemie (International ed. in English) · 2022Article
- Inhibition of Cysteine Proteases by 6,6'-Dihydroxythiobinupharidine (DTBN) fromMolecules (Basel, Switzerland) · 2021Article
- Biomimetic Approaches to the Synthesis of Natural Disesquiterpenoids: An Update.Plants (Basel, Switzerland) · 2021Review
- Recent synthesis of thietanes.Beilstein journal of organic chemistry · 2020Review
- Nuphar alkaloids induce very rapid apoptosis through a novel caspase-dependent but BAX/BAK-independent pathway.Cell biology and toxicology · 2019Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
An asymmetric total synthesis of (+)-6-hydroxythiobinupharidine (1b) and (-)-6-hydroxythionuphlutine (2b), a set of hemiaminal containing dimeric sesquiterpenes isolated from yellow water lilies of the Nuphar genus, is described. The central bis-spirocyclic tetrahydrothiophene ring was forged through the Stevens rearrangement of a sulfonium ylide, generated in situ from the coupling of a copper-carbene with a spirocyclic thietane. This strategy diverges both from the proposed biosynthesis1 and previous syntheses of this family of alkaloids,2,3 all of which employ dimerization of symmetric monomers to form the aforementioned thiaspirane. The coupling of unsymmetrical monomers allowed access to the unsymmetrically oxidized product 2b for the first time.
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