Synthesis of new echinocandin derivatives via a diol-keto transposition

Abstract A new diol-carbonyl transposition reaction has been discovered in echinocandin type structures. An α-hydroxy hemiaminal moiety has been shown to undergo a pinacol-type rearrangement in the presence of trimethylsilyl iodide to afford ketone derivatives. Applied to deoxymulundocandin, this transposition led to a useful intermediate for further chemical modification.