Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene–Alkene [2+2] Cycloadditions and Late‐Stage CH Oxidation |
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| Authors: | Christopher M. Rasik Prof. M. Kevin Brown |
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| Affiliation: | Department of Chemistry, Indiana University, 800 E. Kirkwood Ave, Bloomington, IN 47401 (USA) |
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| Abstract: | The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene–alkene [2+2] cycloaddition and a late‐stage carboxylic acid directed C(sp3)? H oxidation. The synthesis requires only eight steps from norbornadiene. |
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| Keywords: | C H oxidation cycloaddition gracilioether F ketenes total synthesis |
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