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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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AbstractThe 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.
Title: Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene–Alkene [2+2] Cycloadditions and Late‐Stage CH Oxidation
Description:
AbstractThe 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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