Journal of the Chemical Society. Perkin transactions I p. 675 - 679 (1984)
Update date:2022-08-02
Topics:
Baxter, Anthony D.
Roberts, Stanley M.
Wakefield, Basil J.
Woolley, Geoffrey T.
Newton, Roger F.
The threo-2-(cyclopent-2-enyl)-1-(2-oxocyclopentyl)ethanol derivatives (2) and (3) have been converted into (+/-)-prostaglandin I2 methyl ester and its 15-epimer.The route involved halogenoetherification, hydrodehalogenation, Baeyer-Villiger oxidation, and methanolysis, to give the 5-hydroxyprostaglandin I1 derivatives (17) and (18).These hydroxy esters were mesylated, the 11- and 15-hydroxy groups were deprotected, and the resulting 15-epimeric alcohols were separated.The final elimination, accomplished by means of neat 1,8-diazabicyclo<5.4.0>undec-7-ene, gave the required Δ5-olefin with a high degree of regioselectivity, and was stereospecifically trans, giving the required Z-configuration (25).
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