ISSN:
0170-2041
Keywords:
Prostaglandin derivatives
;
Lactones
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201203
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