Serofendic acid

Chemical Name: (4beta,8alpha,10alpha,15beta)-15-Hydroxy-17-(methylsulfinyl)atisan-18-oic acid
项目整合开发状态: Biological Testing
项目研究机构: Eisai (Originator)
合成路线:Serofendic acid has been synthesized starting from the known intermediate (I).Allylic oxidation of exo-olefin (I) with SeO2 yields a mixture of alcohols (II) and (III).Hydroboration of isomer (III),followed by oxidative work-up,gives rise to the target syn-diastereoisomer (IV).Inversion of the C15-hydroxyl group in (IV) is then achieved by selective oxidation of the secondary alcohol with NaBrO3/NaHSO3,followed by NaBH(OAc)3 reduction of the resultant ketone (V) to produce diol (VI).Tosylation of diol (VI) takes place at the primary alcohol group,to furnish tosylate (VII).

合成路线:Displacement of tosylate (VII) with sodium methylsulfide,and simultaneous ester group hydrolysis leads to sulfide (VIII).This is finally oxidized to the corresponding sulfoxide employing Davis oxaziridine.