Abstract
Abstract The enantioselective synthesis of mexiprostil (16R-16-methoxy-16-methyl PGE1 methyl ester) is described. The assembly of the prostaglandin framework has been accomplished by the three component coupling process, via consecutive linking of the ω and α-sidechain to unsubstituted (R)-4-hydroxy-2-cyclopentenone, and alternatively by a conjugate addition of the ω-side chain to a (R)-4-hydroxy-2-cyclopentenone in which the α-side chain is already incorporated. The required lower side chain building block is prepared enantioselectively from nerol utilising the Sharpless epoxidation reaction.
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