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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 33, Number 1
BKCSDE 33(1)
January 20, 2012 

Mild Isomerative Opening of Tetrahydrofuranyl Subunits in Steroids Using TFAT (trifluoroacetyl trifluoromethanesulfonate): Application to Synthesis of C17-OH Rockogenin Acetate
Jong Seok Lee, * Byungsook Kim, Junho Shin, Yeon-Ju Lee, Hee Jae Shin, Hyi-Seung Lee
Steroid, TFAT (trifluoroacetyl trifluoromethanesulfonate), Ring opening, Dihydroxylation, Alkoxyl radical cyclization
A novel and efficient tetrahydrofuranyl ring opening method was developed using the highly reactive TFAT reagent in the presence of an acid scavenger, 2,6-di-tert-butyl-4-methylpyridine. Various acid sensitive groups are 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-OH rockogenin acetate.
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