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E-mail: jslee@kordi.re.krReceived October 20, 2011, Accepted November 2, 2011A novel and efficient tetrahydrofuranyl ring opening method was developed using the highly reactive TFATreagent in the presence of an acid scavenger, 2,6-di- tert-butyl-4-methylpyridine. Various acid sensitive groupsare compatible with the reaction condition, making it generally applicable to many tetrahydrofuranyl steroids.Moreover, it is a synthetic equivalent of ‘Marker degradation’ affording an efficient synthesis of C17-OHrockogenin acetate.Key Words : Steroid, TFAT (trifluoroacetyl trifluoromethanesulfonate), Ring opening, Dihydroxylation,Alkoxyl radical cyclizationIntroductionIn modern organic synthesis, the ether is one of the mostfrequently found features.It is commonly used as a protect-ing group for alcohols.

bulletin of the korean chemical society

Mild Isomerative Opening of Tetrahydrofuranyl Subunits in Steroids Using TFAT (trifluoroacetyl trifluoromethanesulfonate): Application to Synthesis of C17-OH Rockogenin Acetate