55056-56-9Relevant academic research and scientific papers
An effective approach to B-ring aromatization of equilin
Cao, Zhisong,Liehr, Joachim G.
, p. 145 - 155 (2007/10/03)
Epoxidation of equilin followed by rearrangement-elimination catalyzed by either proton acids or Lewis acids generates an estrogen with an aromatic B-ring. This procedure represents an effective method for the conversion of an equilin nucleus to an equilenin nucleus.
SYNTHESIS OF 2-METHOXY AND 4-METHOXY EQUINE ESTROGENS
Pemmaraju, N. Rao,Somawardhana, Chandrasiri W.
, p. 419 - 432 (2007/10/02)
4-Methoxyequilin and 2-methoxyequilin were synthesized from the corresponding 4-bromoequilin and 2-iodoequilin derivatives, respectively, by nucleophilic displacement of halogen with methoxide ion in the presence of copper(II)chloride and 15-crown-5-ether. 4-Bromoequilin was prepared by reacting equilin with one equivalent of N-bromoacetamide. 2-Iodoequilin was prepared by reductive dehalogenation of 2,4-diiodoequilin, which in turn was obtained by treatment of equilin with two equivalents of iodine in methanolic ammonium hydroxide solution. 4-Methoxyequilenin and 2-methoxyequilenin were prepared from the corresponding 4-iodo- and 2-iodo-7ξ,8ξ-epoxyestrone derivatives, respectively.Nucleophilic displacement of iodine with methoxide ion was carried out as described earlier with simultaneous aromatization of the B ring leading to 4- and 2-methoxyequilenin derivatives.Alternatively, 4-methoxyequilenin was obtained from 4-methoxyequilin by selenium dioxide oxidation.
