Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate ß,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,ß-enals.

ABSTRACT

A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate ß,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,ß-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.