Unsaturated fatty acids are known to demonstrate desirable antibacterial activity; Ieodomycins A and B are no exception. Derived from marine <i>Bacillus</i> sp., these natural products have demonstrated activity against Gram-positive and Gram-negative pathogens. Koul and co-workers were the first to completea the total syntheses of Ieodomycins A and B in fifteen steps using a chiral pool approach from ᴅ-glucose. The shortest route to date by Meshram and involves eight steps including an Evans aldol reaction and nucleophilic addition of potassium salt of mono methyl malonate. A convergent asymmetric vinylogous-aldol strategy has been studied for this target-oriented synthesis due to the similarities between these natural products. A series of reactions including carboalumination, Suzuki coupling, IBX oxidation have been successfully performed to synthesize the requisite aldehyde, while a silyl-ketene acetal formation has been carried out to create the procarbonyl donor synthon. As proposed, this strategy would decrease the total number of steps to six for the longest linear sequence. Future directions include: optimizing conditions to improve the yield of asymmetric aldol reaction, exploring different ligands for enhanced asymmetric induction, and attempting end-game functional group interconversions. Finally, a full biological evaluation would be applied to fully evaluate their biological activities.

Progress toward the enantioselective total syntheses of Ieodomycins A and B via an asymmetric vinylogous aldol strategy

249th National Meeting (2015)

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