Synthesis of Wailupemycins B

Significance

Wailupemycins A and B inhibited the growth of E. coli in preliminary experiments. Both compounds feature highly substituted cyclohexanone rings making them challenging synthetic targets. They differ in configuration at C-7, which allows acetal formation to occur in Wailupemycin B only. Two approaches are described which failed at the stage of addition to a carbonyl. Wailupemycin B was eventually synthesized confirming the relative and absolute stereochemistry of the compound.