ChemInform Abstract: Carbocycles from Carbohydrates: A Simple Route to an Enantiomerically Pure Prostaglandin Intermediate.

ChemInform Abstract

The dihydroxy(hydroxymethyl)lactone (I) is converted to the methylenelactone (V) which is reductively rearranged and then dehydrated, yielding the cyclopentenone (VII). (V) and phenylmagnesium bromide (VIII) produce the carbinol (IX) which is dehydrated, forming the cyclopentenone (X). The cyclopentenones, obtained in enantiomerically pure form, are intermediates in the synthesis of prostaglandins.