ONO-8815

Chemical Name: 9-Chloro-9,15-dideoxy-16(S)-(1-ethylcyclobutyl)-16-hydroxy-17,18,19,20-tetranorprostaglandin F2beta
CAS No. 212311-08-5
项目整合开发状态: Preclinical
项目研究机构: Ono (Originator)
合成路线:Protection of (I) with TBDMSCl in DMF in presence of imidazole affords (II) which is then converted into iodo derivative (III) by first treatment with AIBN in presence of n-Bu3SnH followed by iodination with I2 in CH2Cl2.The reaction of (III) with derivative (IV) in presence of t-BuLi in pentane and lithium 2-thienylcyanocuprate in THF yields methyl ester (Va-b) which is then reduced with L-Selectride in THF to afford (VIa-b).Treatment of (VIa-b) with TsCl provides tosylated derivative (VIIa-b) which suffers a nucleofilic attack by tetrabutylammonium chloride yielding (VIIIa-b).Finally TBDMS groups of (VIIIa-b) are removed by treatment with hydrofluoric acid in CH3CN and the methyl ester group hydrolised by means of NaOH in MeOH.