Rioprostil, TR-4698, ORF-15927

利奥前列素Chemical Name: (11alpha,13E)-1,11,16-Trihydroxy-16-methylprost-13-en-9-one; (2R,3R,4R)-4-Hydroxy-2-(7-hydroxyheptyl)-3-[(E)-(4RS)-(4-hydroxy-4-methyl-1-octenyl)]cyclopentanone
CAS No. 77287-05-9
项目整合开发状态: Phase III
项目研究机构: Bayer (Originator), Ortho-McNeil (Originator)
合成路线:The Grignard reaction of propargylmagnesium bromide (I) with 2-hexanone (II) in ether gives 4-methyloct-1-in-4-ol (III),which by reaction with diisobutylaluminum hydride and I2 is converted to 1-iodo-4-methyloct-1-en-4-ol (IV).The reaction of (IV) with dihydropyran and p-toluenesulfonic acid yields the corresponding tetrahydropyranyloxy derivative (V),which by reaction with tert-butyllithium and copper pentyne (VI) affords the corresponding organolithiocuprate (VII).The condensation of (VII) with 4R-(tetrahydropyranyloxy)-2-[7-(tetrahydropyranyloxyl)heptyl]cyclopent-2-en-1-one (VIII) in ether gives 1,11,16-tris(tetrahydropyranyloxy)-16-methylprost-13-en-9-one (IX),which is finally deprotected by a treatment with acetic acid in water THF.