Facile and Efficient Synthesis of Lactols by a Domino Reaction of 2,3-Epoxy Alcohols with a Hypervalent Iodine (III) Reagent and Its Application to the Synthesis of Lactones and the Asymmetric Synthesis of (+)-Tanikolide

摘要

The domino reaction of 2,3-epoxy-1-alcohol derivatives,namely tetrasubstituted 2,3-epoxy-1-alcohols and 2- or 3-alkyl trisubstituted 2,3-epoxy-l-alcohols,with PhI(OCOCF3)2 in the presence of H2O is described in detail.In this reaction,several types of lactol derivatives can be directly obtained from the 2,3-epoxy-1-alcohol derivatives in a single operation.The obtained lactols were successively converted into the corresponding lactones.This reaction is applicable to the construction of optically active lactone compounds.The asymmetric total synthesis of (+)-tanikolide,an antifungal marine natural product,has been effectively achieved by using this reaction.