Intramolecular Nitrile Oxide Cycloaddition Route to Carbocyclics: A Formal Total Synthesis of PGF2α

Article abstract of DOI:10.1021/jo00187a001

A formal total synthesis of the prostaglandin F_2α is reported which is based on the reaction of a nitrile oxide, generated by th sodium hypochlorite oxidation of an oxime, with a tethered olefin.The present study reveals the importance of an existing ring structure to control both the kinetics and the stereochemical course of the cycloaddition process.The possibility of carrying out the present synthesis in a chiral-selective fashion through employment of a chiral epoxide is also discussed.