Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

An interesting transformation during the oxidation of 3,4-epoxy alcohols , derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls in very good yields. One of these products was transformed into the functionalised carboxylic acid , an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported.