The Journal of Organic Chemistry

Intramolecular nitrile oxide cycloaddition route to carbocyclics: a formal total synthesis of PGF2. alpha.

AP Kozikowski, PD Stein

Index: Kozikowski, Alan P.; Stein, Philip D. Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2301 - 2309

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Citation Number: 92

Abstract

A formal total synthesis of the prostaglandin Fzo, is reported which is baed on the reaction of a nitrile oxide, generated by the 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 ...

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