Total Synthesis of the Marine Polyketide (-)-Gracilioether F

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  • Department of Organic Chemistry, Indian Association for the Cultivation of Science


First asymmetric synthesis of the marine natural product (-)-gracilioether F is described from a d-mannitol derived known compound. The key step involves intramolecular 1,4-conjugate addition of a hydroxymethyl radical generated from Ti (III) mediated ring opening of a terminal epoxy ring tethered to a butenolide to produce stereoselectively a five-membered ring fused bicyclic lactone, the core structure present in gracilioether F.


Original languageEnglish
Pages (from-to)7675-7682
Number of pages8
JournalThe Journal of Organic Chemistry
Issue number14
Publication statusPublished - 21 Jun 2017


  • Journal Article