Total synthesis of the macrodiolide pyrenophorol

Article abstract of DOI:10.1016/0040-4039(91)80368-G

By means of a total synthesis, the absolute configuration of the naturally occurring macrodiolide pyrenophorol has been established. An essential step is the photo-induced rearrangement of an α,β-epoxy diazomethyl ketone to produce a 4-hydroxy-2-alkenoate. The two lactone units have been introduced in two successive steps.