The oxidation of the 3β-hydroxy group in the steroidal substrates obtained from naturally occurring sources, i.e., solanaceae steroidal sapogenins, is an important process in the preparation of ecdysteroid analogs. The need for selective green oxidation methodologies for steroidal alcohols (spirostenols, diosgenine, and derivatives) avoid the use of toxic Cr (VI) derivatives, without the isomerization of the double bond at 5,6 position and also without the oxidative cleavage of the spirocetal moiety is of great methodological significance. Herein, we report the oxidation of spirostanic steroidal alcohols to their carbonyl analogs using hypervalent iodine (III)/TEMPO-4-N-acetoxyamine system. The present method is simple, eco-sustainable, efficient, and high-yielding process for the oxidative transformation of secondary steroidal alcohols without any over-oxidation, isomerization of the double bond, or oxidative cleavage of spirocetalic fragment in different substrates. Therefore, this method does not involve toxic heavy metals and is expected to have wide utility in the oxidation process of these compounds.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.