PGE-3366466

Chemical Name: 7-[(1R,2R,3R,5S)-2-[3(R)-(Benzo[b]thien-2-yl)-3-hydroxypropyl]-3,5-dihydroxycyclopentyl]heptanoic acid; 15-(2-Benzothienyl)-13,14-dihydro-16,17,18,19,20-pentanorprostaglandin F1alpha
项目整合开发状态: Preclinical
项目研究机构: Procter & Gamble (Originator)
合成路线:Methyl (R)-7-(3-hydroxy-5-oxo-1-cyclopent-1-yl)heptanoate (I) was protected as the silyl ether (II) using tert-butyldimethylsilyl triflate and 2,6-lutidine.Conjugate addition to (II) of the organocuprate reagent derived from butenylmagnesium bromide (III) and CuBr produced adduct (IV).Reduction of the keto group of (IV) with NaBH4,followed by silylation of the resulting alcohol (V),furnished the bis-silyl ether (VI).Subsequent olefin oxidative cleavage by means of potassium osmate and sodium periodate gave rise to aldehyde (VII).To this was added 2-lithiobenzothiophene (VIII) to yield carbinol (IX).Desilylation of (IX) to triol (X) was then achieved by using HF in pyridine.The methyl ester group of (X) was finally hydrolyzed with LiOH to give the title carboxylic acid.