trans-Hydroxylation of cyclopent-5-ene[d]isoxazolines

Abstract

The title reaction has been studied as a variant of the cyclopentane ring functionalization of cyclopent-5-ene[d]isoxazolines as the key intermediates in total synthesis of azaand oxo prostaglandin analogues by nitrileoxides approach. The oxidation, epoxides cleavage and hydrolysis of obtained monoesters and/or acylation lead with good yields to trans-5,6-dihydroxycyclopentanoisoxazolines or their acyl derivatives. The synthesized substances are the intermediates in total synthesis of prostaglandin analogues, as well as perspective biologically active compounds.