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http://dx.doi.org/10.5012/bkcs.2012.33.1.76

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

Lee, Jong-Seok (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
Kim, Byung-Sook (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
Shin, Jun-Ho (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
Lee, Yeon-Ju (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
Shin, Hee-Jae (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
Lee, Hyi-Seung (Marine Natural Products Laboratory, Korea Ocean Research and Development Institute)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.1, 2012 , pp. 76-82 More about this Journal
Abstract
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.
Keywords
Steroid; TFAT (trifluoroacetyl trifluoromethanesulfonate); Ring opening; Dihydroxylation; Alkoxyl radical cyclization;
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