{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T10:09:45Z","timestamp":1760609385530,"version":"build-2065373602"},"reference-count":34,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2021,6,24]],"date-time":"2021-06-24T00:00:00Z","timestamp":1624492800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100007336","name":"University of Bucharest","doi-asserted-by":"publisher","award":["UniRem project no. 244 and the contract CNFIS-FDI-2020-0355."],"award-info":[{"award-number":["UniRem project no. 244 and the contract CNFIS-FDI-2020-0355."]}],"id":[{"id":"10.13039\/501100007336","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100015622","name":"Ministerul Cercet\u0103rii \u015fi Inov\u0103rii","doi-asserted-by":"publisher","award":["grant Orizont-2000, 45\/1999\/1"],"award-info":[{"award-number":["grant Orizont-2000, 45\/1999\/1"]}],"id":[{"id":"10.13039\/501100015622","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>\u03b2-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 15\u03b1-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.<\/jats:p>","DOI":"10.3390\/ijms22136787","type":"journal-article","created":{"date-parts":[[2021,6,24]],"date-time":"2021-06-24T11:01:38Z","timestamp":1624532498000},"page":"6787","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["\u03b2-Ketophosphonates with Pentalenofuran Scaffolds Linked to the Ketone Group for the Synthesis of Prostaglandin Analogs"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3867-1064","authenticated-orcid":false,"given":"Constantin I.","family":"T\u0103nase","sequence":"first","affiliation":[{"name":"National Institute for Chemical-Pharmaceutical Research and Development-ICCF, 112 Vitan Av., 031299 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Constantin","family":"Dr\u0103ghici","sequence":"additional","affiliation":[{"name":"Organic Chemistry Center \u201cC.D.Nenittescu\u201d, 202B, Splaiul Independentei, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miron Teodor","family":"C\u0103proiu","sequence":"additional","affiliation":[{"name":"Organic Chemistry Center \u201cC.D.Nenittescu\u201d, 202B, Splaiul Independentei, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0433-752X","authenticated-orcid":false,"given":"Anamaria","family":"Hanganu","sequence":"additional","affiliation":[{"name":"Organic Chemistry Center \u201cC.D.Nenittescu\u201d, 202B, Splaiul Independentei, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gheorghe","family":"Borodi","sequence":"additional","affiliation":[{"name":"National Institute for R&D of Isotopic and Molecular Technologies, 67-103 Donat, 400293 Cluj-Napoca, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria","family":"Maganu","sequence":"additional","affiliation":[{"name":"Organic Chemistry Center \u201cC.D.Nenittescu\u201d, 202B, Splaiul Independentei, 060023 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emese","family":"Gal","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Aranyl\u00e1nos 11, 400012 Cluj-Napoca, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1036-7653","authenticated-orcid":false,"given":"Lucia","family":"Pintilie","sequence":"additional","affiliation":[{"name":"National Institute for Chemical-Pharmaceutical Research and Development-ICCF, 112 Vitan Av., 031299 Bucharest, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,6,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1533","DOI":"10.1021\/cr00020a007","article-title":"Synthesis of Therapeutically Useful Prostaglandin and Prostacyclin Analogs","volume":"93","author":"Collins","year":"1993","journal-title":"Chem. 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