Tetrahedron p. 3807 - 3820 (1983)
Update date:2022-07-30
Topics:
Bannai, Kiyoshi
Toru, Takeshi
Oba, Takeo
Tanaka, Toshio
Noriaki, Okamura
et al.
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.
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Doi:10.1139/v82-038
(1982)Doi:10.1021/ol0479040
(2004)Doi:10.1021/jo00264a024
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(1982)