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- W2034900855 abstract "Two short synthetic routes to the major metabolites of prostaglandins in man are reported. First, the 2,3,4,5-tetranorprostaglandins 1 and 2 are readily accessible by one-carbon homologation of γ-lactone 8 which involves the use of an ylide reagent, prepared from (1,3-dithian-2-yl)triphenylphosphonium chloride (9), subsequent cyclization of thioketene S,S-acetal 10 to spirotricyclic 11, and desulfurization to yield the required δ-lactone 12. Second, 6-oxoprostaglandins 3 and 4 are conveniently synthesized via α-acylation of the enolates of γ-lactones such as 22 followed by deprotection, hydrolysis, and decarboxylation of the resultant 3-oxocarboxylic acids. Both approaches have been realized with the synthesis of deuterated, racemic analogues of the prostaglandin metabolites." @default.
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- W2034900855 date "1992-12-22" @default.
- W2034900855 modified "2023-09-25" @default.
- W2034900855 title "Novel Syntheses of 2,3,4,5-Tetranor- and 6-oxo-Prostaglandins" @default.
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- W2034900855 doi "https://doi.org/10.1002/jlac.1992199201203" @default.
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