SYNTHESIS OF CHEMICALLY STABLE PROSTACYCLIN ANALOGS

DOI: 10.1016/S0040-4020(01)88623-3

Source and publish data:

Tetrahedron p. 3807 - 3820 (1983)

Update date:2022-07-30

Topics:

Authors:

Bannai, Kiyoshi

Toru, Takeshi

Oba, Takeo

Tanaka, Toshio

Noriaki, Okamura

et al. et al.

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Article abstract of DOI:10.1016/S0040-4020(01)88623-3

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.

Full text of DOI:10.1016/S0040-4020(01)88623-3

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