Synthesis of the four isomers of 5-hydroxy-PGI1 |
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Authors: | John C Sih Roy A Johnson Eldon G Nidy David R Graber |
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Institution: | Experimental Chemistry Research, The Upjohn Company, Kalamazoo, Michigan 49001, USA |
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Abstract: | We wish to report here the syntheses of (5, 6)-5-hydroxy-, (5, 6)-5-hydroxy-, (5, 6)-5-hydroxy-, and (5, 6)-5-hydroxy-PGI1 and their methyl ester derivatives. Treatment of (5, 6)-5-epoxy- and (5, 6)-5-epoxy-PFG1α methyl esters with acid washed silica gel afforded (5, 6)-5-hydroxy- and (5, 6)-5-hydroxy-PGI1 methyl esters; correspondingly, silica promoted cyclization of (5, 6)-epoxy- and (5, 6)-5-epoxy- PGF1 methyl esters yielded (5, 6)-5-hydroxy- and (5, 6)-5-hydroxy- PGI1 methyl esters. Alternatively, the 5-hydroxyl group was introduced into the PGI1 skeleton reaction of the 5-mercuric halides with sodium borohydride in the presence of oxygen. Stereochemical assignments were based on their mode of synthesis and 1H nmr shift differences. |
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