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Synthesis of Methoxyfumimycin with 1,2-Addition to Ketimines

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journal contribution
posted on 01.01.2010, 00:00 by Patrick J. Gross, Caroline E. Hartmann, Martin Nieger, Stefan Bräse
The synthesis of (±)-methoxyfumimycin, a potential new bacterial peptide deformylase (PDF) inhibitor, is reported. To generate the stereogenic fully substituted carbon, the key step is a 1,2-addition of a methyl Grignard reagent to a ketimine. The overall synthetic strategy involves a Dakin oxidation of a vanillin derivative, Friedel−Crafts acylation, Claisen rearrangement, lactonization, and rhodium-catalyzed olefin isomerization.