新产品编号:2477921

Chemical Name: 2-Methoxyestra-1,3,5(10),14-tetraene-3,17beta-diol; 14-Dehydro-2-methoxyestradiol
项目整合开发状态: Preclinical
项目研究机构: Southwest Foundation for Biomedical Res. (Originator)
合成路线:The known 17-hydroxy steroid (I) is oxidized to the corresponding ketone (II) by means of the Jones reagent in acetone.After protection of the ketone (II) as the ethylidene ketal (III),removal of the 3-benzyl ether under transfer hydrogenation conditions furnishes the phenol (IV),which is esterified with acetic anhydride in pyridine to give the aryl acetate (V).Bromination at the alpha-position of the ketalized keto group of (V) is carried out in the presence of phenyltrimethylammonium tribromide in cold THF to produce the 16-alpha-bromide (VI).Dehydrobromination of (VI) with simultaneous acetate hydrolysis upon treatment with potassium tert-butoxide leads to the olefin (VII).Subsequent acidic hydrolysis of ketal (VII) gives the enone (VIII),which is further acylated with isopropenyl acetate and acetic anhydride in the presence of p-toluenesulfonic acid to furnish the dienyl acetate (IX).Finally,reductive treatment of (IX) with sodium borohydride affords the target diol.