Diastereoselective synthesis of protected syn 1,3-Diols: Preparation of the C16-C24 portion of dolabelides

Abstract : (Equation Presented) We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.