Abstract
β-Ketophosphonates with pentalenofurane fragments linked to the keto group were synthesized. The bulky pentalenofurane skeleton is expected to introduce more hindrance in the prostaglandin analogues of type III, greater than that obtained with the bicyclo[3.3.0]oct(a)ene fragments of prostaglandin analogues I and II, to slow down (retard) the inactivation of the prostaglandin analogues by oxidation of 15α-OH to the 15-keto group via the 15-PGDH pathway. Their synthesis was performed by a sequence of three high yield reactions, starting from the pentalenofurane alcohols 2, oxidation of alcohols to acids 3, esterification of acids 3 to methyl esters 4 and reaction of the esters 4 with lithium salt of dimethyl methanephosphonate at low temperature. The secondary compounds 6b and 6c were formed in small amounts in the oxidation reactions of 2b and 2c, and the NMR spectroscopy showed that their structure is that of an ester of the acid with the starting alcohol. Their molecular structures were confirmed by single crystal X-ray determination method for 6c and XRPD powder method for 6b.
Highlights
IntroductionPublisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations
For theand synthesis of new β-ketophosphonates, the key step was the reaction of an ester
[21,22,23]; ester with the lithium salt of dimethyl methanephosphonate, like in the previous papers ester with the lithium saltare ofkey dimethyl methanephosphonate, like in thechain previous papers the β-ketophosphonates intermediates for building the ω-side in the total stereocontrolled convergent synthesis of prostaglandins and we have used them for obtaining the intermediates used further in the hydrogenation of the double bond of the ω-side chain [24]
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. 2-indanyl [19], aryl or heteroaryl scafolds [20] are claimed in patents. In this direction, we introduced bicyclo[3.3.0]octene or bicylo[3.3.0]octane fragments in the β-ketophosphonates used to build the ω-side chain in a selective E-Horner- Wadsworth. 1. Prostaglandin analogs of type respectively ofof typeIIIwith withaaabicyclo[3.3.0]octene bicyclo[3.3.0]octenefragment fragmentand and respectively
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