Tosagestin, ORG-30659

(8R,9S,10R,13S,14S,17R)-17-乙炔基-17-羟基-13-甲基-11-亚甲基-2,6,7,8,9,10,12,14-八氢-1H-环戊二烯并[a]菲-3-酮Chemical Name: 17alpha-Ethynyl-17beta-hydroxy-11-methyleneestra-4,15-dien-3-one; (17alpha)-17-Hydroxy-11-methylene-19-norpregna-4,15-dien-20-yn-3-one
CAS No. 110072-15-6
项目整合开发状态: Phase II
项目研究机构: Organon (Originator)
合成路线:The incubation of 11-methyleneestr-4-ene-3,17-dione (I) with spores of Gomerella cingulata (ATCC 10534) gives 15-alpha-hydroxy-11-methyleneestr-4-ene-3,17-dione (II),which is treated with ethane-1,2-dithiol and borontrifluoride ethearate in ethanol yielding the 3-dithioacetal (III).The reaction of (III) with methanesulfonyl chloride,followed by elimination with sodium acetate affords 11-methyleneestra-4,15-diene-3,17-dione 3-(ethylenedithioacetal) (IV),which is treated with potassium acetylide (V) in THF to afford the 17-alpha-ethynyl-17-beta-hydroxy derivative (VI).Finally,this compound is deprotected by a treatment with K2CO3 and methyl iodide in refluxing methanol/water.