ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Isolation and Characterization of the Cyanobacterial Macrolide Glycoside Moorenaside, an Anti-Inflammatory Analogue of Aurisides Targeting the Keap1/Nrf2 Pathway.Journal of natural products · 2024Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Recent applications of dioxinone derivatives for macrocyclic natural product and terpenoid synthesis.Frontiers in chemistry · 2022Review
- Bifunctional Doscadenamides Activate Quorum Sensing in Gram-Negative Bacteria and Synergize with TRAIL to Induce Apoptosis in Cancer Cells.Journal of natural products · 2021Article
- Antimalarial Peptide and Polyketide Natural Products from the Fijian Marine CyanobacteriumMarine drugs · 2020Article
- Conformation-guided analogue design identifies potential antimalarial compounds through inhibition of mitochondrial respiration.Organic & biomolecular chemistry · 2018Article
- A Review Study on Macrolides Isolated from Cyanobacteria.Marine drugs · 2017Review
- Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon.Frontiers in chemistry · 2016Article
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Authors and funding
3 authors.
Funding
Abstract
Lyngbyaloside C, a classic macrolide, isolated from Lyngbya bouilloni, has shown moderate anticancer activity against several cancer cell lines. Here, we report the first total synthesis and stereochemical configuration reassignment of lyngbyaloside C. The synthesis highlights a one-pot intermolecular ketene esterification reaction to form the crucial tertiary ester and tetrahydropyran. In addition, a novel and concise synthetic pathway towards the 1,3-syn secondary, tertiary diol fragment is described using a regio- and stereospecific electrophilic ether transfer reaction.
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