89682-83-7Relevant academic research and scientific papers
SYNTHESIS OF CHEMICALLY STABLE PROSTACYCLIN ANALOGS
Bannai, Kiyoshi,Toru, Takeshi,Oba, Takeo,Tanaka, Toshio,Noriaki, Okamura,et al.
, p. 3807 - 3820 (2007/10/02)
Syntheses of several stable PGI2 analogs substituted by an electron-withdrawing substituent at C-5 or C-7 are described.Reaction of PGI2 methyl ester (1) with benzenesulfenyl chloride gave (5E)-5-phenylthio-PGI2 (2) or (5R)-5-phenylthio-Δ6-PGI1 (5) according to the reaction condition employed.Allyl sulfide 5 was transformed into (7S)-7-hydroxy-PGI2 (11) and (7S)-7-acetoxy PGI2 (12) via stereocontrolled sulfoxide-sulfenate rearrangement, and alcohol 11 was further transformed into (7S)-7-fluoro-PGI2 (14).These PGI2 analogs were found much more stable than PGI2.
