Current time in Korea 22:21 Oct 23 (Mon) Year 2017 KCS KCS Publications
KCS Publications
My Journal Log In Register
HOME > Search > Browsing(BKCS) > Archives

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 

 
Title
Mild Isomerative Opening of Tetrahydrofuranyl Subunits in Steroids Using TFAT (trifluoroacetyl trifluoromethanesulfonate): Application to Synthesis of C17-OH Rockogenin Acetate
Author
Jong Seok Lee, * Byungsook Kim, Junho Shin, Yeon-Ju Lee, Hee Jae Shin, Hyi-Seung Lee
Keywords
Steroid, TFAT (trifluoroacetyl trifluoromethanesulfonate), Ring opening, Dihydroxylation, Alkoxyl radical cyclization
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.
Page
76 - 82
Full Text
PDF