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Total Synthesis of the Marine Polyketide (-)-Gracilioether F
Ritabrata Datta1, Subrata Ghosh1
1Department of Organic Chemistry, Indian Association for the Cultivation of Science , Jadavpur, Kolkata 700 032, India.
Abstract:
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.
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