Practical semisynthesis of equilenin and its derivatives
Equilenin 2 and its derivatives are important intermediates in the synthesis of steroidal drugs. Until now, these estrogens were produced by extraction from pregnant mare's urine due to the lack of efficient synthetic methods. Most reported semisyntheses of equilenin involve expensive raw materials or toxic reagents to suppress undesired epimerization at C/D ring juncture. Herein, we reported a practical synthesis of highly pure equilenin and its derivatives from an easily available raw material 6 with conventional reagents.
Yue, Tao,Li, Hong-Ping,Ding, Kai
p. 4850 - 4853
(2016/10/07)
Alcohol inversion of 17β-steroids
Inversion of 17β-steroids has been accomplished using a modified Mitsunobu protocol in which 4-nitrobenzoic acid is employed as the acidic component. Excellent yields of inverted product were obtained for a number of representative steroid families including estrogens, equilenins, and androgens. Application of this methodology to the synthesis of 17α-dihydroequilenin is described.
Dodge, Jeffrey A.,Lugar III, Charles W.
p. 1 - 2
(2007/10/03)
B-ring aromatization of estrogen derivatives
A noval method of B-ring aromatization of steroid derivatives is reported. Addition of BrCl in methanol to a non-aromatic B-ring double bond results in a rapid double elimination generating the aromatic B-ring. This procedure represents an effective method for conversion of an equilin to an equilenin nucleus.
Hylarides,Wilbur,Mettler Jr.
p. 657 - 662
(2007/10/02)
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