Prostaglandins and prostaglandin intermediates. XV. Synthesis of 4‐Oxo Carboxylic Acids and γ‐Lactones by oxidative cleavage of homoallyl and homopropargyl ketones or alcohols

Abstract

AbstractA convenient method to convert homoallyl or homopropargyl ketones or alcohols into 4‐oxo carboxylic acids or γ‐lactones is the oxidative cleavage of the multiple bond with potassium permanganate in diluted sulfuric acid. This is exemplified by the preparation of intermediates for the synthesis of 8‐methylprostaglandin C2. The oxidation of the allylic compounds with permanganate is compared with the oxidative cleavage by ozone/hydrogen peroxide, ozone/chromic acid or sodium periodate/potassium permanganate.