Preparation and Utilization of Chiral alpha-and beta-Hydroxyacetylenes

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Some chiral acetylene building blocks having hydroxy functionality on alpha- or beta-stereogenic center have been prepared in efficient manners involving enzymatic reaction using lipase and asymmetric reaction employing the Katsuki-Sharpless asymmetric epoxidation reaction.Versatile utility of these acetylene derivatives as chiral building blocks has been demonstrated by transforming these into a wide variety of natural product ranging from simple monoterpenoids to complex natural products, such as alkaloids, aminoacids, and poly ketides in enantiocontrolled ways as well as by devising specific reactions making use of these chiral acetylene compounds.