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• W2109334517 endingPage "4533" @default.
• W2109334517 startingPage "4529" @default.
• W2109334517 abstract "A concise approach to the algal metabolite 1 is described, which also determines the previously unknown stereostructure of this natural product. Compound 1 is distinguished by a rare brominated 4-pyrone nucleus linked as a ketene–acetal to a polyunsaturated macrocyclic scaffold comprising an extra homoallylic bromide entity. The synthesis of 1 is based on the elaboration and selective functionalization of the linear precursor 23 endowed with no less than six different sites of unsaturation including the highly enolized oxo-alkanoate function. Key to success was the formation of the 2-alkoxy-4-pyrone ring by a novel gold-catalyzed transformation which engages only the acetylenic β-ketoester substructure of 23 but leaves all other π-bonds untouched. The synthesis was completed by a ring-closing alkyne metathesis to forge the signature cycloalkyne motif of 1 followed by selective bromination of the ketene–acetal site in the resulting product 27 without touching the skipped diene–yne substructure resident within the macrocyclic tether." @default.
• W2109334517 created "2016-06-24" @default.
• W2109334517 creator A5024154682 @default.
• W2109334517 creator A5054667122 @default.
• W2109334517 creator A5077339413 @default.
• W2109334517 creator A5087975726 @default.
• W2109334517 date "2015-02-25" @default.
• W2109334517 modified "2023-09-30" @default.
• W2109334517 title "Total Synthesis of an Exceptional Brominated 4-Pyrone Derivative of Algal Origin: An Exercise in Gold Catalysis and Alkyne Metathesis" @default.
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• W2109334517 doi "https://doi.org/10.1002/chem.201500437" @default.
• W2109334517 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25712698" @default.
• W2109334517 hasPublicationYear "2015" @default.
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