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Novel Syntheses of 2,3,4,5-Tetranor- and 6-oxo-Prostaglandins

✍ Scribed by Meese, Claus O.

Book ID
102903203
Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
802 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

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.

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