Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative

The Wittig reaction of {(1S,4R,5R)-5-[(tert-butyldimethylsilyloxy) methyl]-4-hydroxycyclopent-2-en-1-yl}acetaldehyde is accompanied by the migration of silyl protective group from the primary hydroxy group to the secondary one, which enables further synthesis of J-type prostaglandins. Study of this phenomemon on model relative ester comprising base variation revealed formation of unusual functionalized bicyclo[3.1.0]hex-2-ene-6-carboxylate derivative.