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Lett."},{"key":"ref23\/cit23b","first-page":"642","author":"Imagawa H.","year":"2006","journal-title":"Synlett"},{"key":"ref24\/cit24","unstructured":"Pd-catalyzed:"},{"key":"ref24\/cit24a","doi-asserted-by":"crossref","first-page":"3937","DOI":"10.1016\/S0040-4020(99)00115-5","volume":"55","author":"Picquet M.","year":"1999","journal-title":"Tetrahedron"},{"key":"ref25\/cit25","unstructured":"Au-catalyzed:"},{"key":"ref25\/cit25a","doi-asserted-by":"crossref","first-page":"7679","DOI":"10.1021\/jo0510585","volume":"70","author":"Yao T.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref25\/cit25b","doi-asserted-by":"crossref","first-page":"11164","DOI":"10.1021\/ja0466964","volume":"126","author":"Yao T.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25c","first-page":"1962","author":"Liu X.","year":"2006","journal-title":"Synlett"},{"key":"ref26\/cit26","unstructured":"Cu-catalyzed:"},{"key":"ref26\/cit26a","doi-asserted-by":"crossref","first-page":"4531","DOI":"10.1021\/jo050191u","volume":"70","author":"Patil N. T.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref27\/cit27","unstructured":"Pd-catalyzed:"},{"key":"ref27\/cit27a","doi-asserted-by":"crossref","first-page":"4139","DOI":"10.1016\/j.tet.2004.03.060","volume":"60","author":"Aurrecoechea J. M.","year":"2004","journal-title":"Tetrahedron"},{"key":"ref28\/cit28","unstructured":"For electrophilic cyclizations leading to of 3-halofurans and 5-halofuropyrimidine nucleosides, see:"},{"key":"ref28\/cit28a","author":"Sniady A.","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"ref28\/cit28b","doi-asserted-by":"crossref","first-page":"1769","DOI":"10.1021\/ol050372i","volume":"7","author":"Sniady A.","year":"2005","journal-title":"Org. Lett."},{"key":"ref28\/cit28c","doi-asserted-by":"crossref","first-page":"6788","DOI":"10.1021\/jo0345648","volume":"68","author":"Rao M. S.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref29\/cit29a","doi-asserted-by":"crossref","first-page":"4405","DOI":"10.1016\/0040-4039(95)00785-B","volume":"36","author":"Vieser R.","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref29\/cit29b","doi-asserted-by":"crossref","first-page":"3387","DOI":"10.1016\/0040-4039(96)00553-9","volume":"37","author":"Arcadi A.","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref29\/cit29c","doi-asserted-by":"crossref","first-page":"15253","DOI":"10.1016\/S0040-4020(98)00953-3","volume":"54","author":"Arcadi A.","year":"1998","journal-title":"Tetrahedron"},{"key":"ref30\/cit30a","doi-asserted-by":"crossref","first-page":"1845","DOI":"10.1351\/pac198355111845","volume":"55","author":"Utimoto K.","year":"1983","journal-title":"Pure Appl. Chem."},{"key":"ref30\/cit30b","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1055\/s-1987-28157","author":"Sheng H.","year":"1987","journal-title":"Synthesis"},{"key":"ref30\/cit30c","doi-asserted-by":"crossref","first-page":"5816","DOI":"10.1021\/jo00020a024","volume":"56","author":"Fukuda Y.","year":"1991","journal-title":"J. Org. Chem."},{"key":"ref31\/cit31","unstructured":"(1-Ethynylcyclopropyl)alkynones:"},{"key":"ref31\/cit31a","doi-asserted-by":"crossref","first-page":"6704","DOI":"10.1002\/anie.200601252","volume":"45","author":"Zhang J.","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref32\/cit32","first-page":"57","author":"M\u00e9nard D.","year":"2006","journal-title":"Synlett"},{"key":"ref33\/cit33","unstructured":"See, for example:"},{"key":"ref33\/cit33a","first-page":"3117","author":"Ermolat\u2019ev D. 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J."},{"key":"ref35\/cit35c","first-page":"519","volume-title":"Transition Metals for Organic Synthesis","author":"Jacobi von Wangelin A.","year":"2003"},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"2331","DOI":"10.1021\/ol006095r","volume":"2","author":"Aschwanden P.","year":"2000","journal-title":"Org. Lett."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"2803","DOI":"10.1021\/ol060896y","volume":"8","author":"Nakamura M.","year":"2006","journal-title":"Org. Lett."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1007\/BF02537126","volume":"28","author":"Pasha M. K.","year":"1993","journal-title":"Lipids"},{"key":"ref39\/cit39","unstructured":"A similar trend was observed when finely ground solids of ZnI2, ZnBr2, or ZnCl2were added. Despite stirring at room temperature for 24 h, such systems remained heterogeneous."},{"key":"ref40\/cit40","unstructured":"For reaction leading to dihydroisoxazole ZnI2was the most effective.(36)"},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"2995","DOI":"10.1021\/jo00216a038","volume":"50","author":"Mayr H.","year":"1985","journal-title":"J. Org. Chem."},{"key":"ref42\/cit42","volume-title":"The Electronic Encyclopedia of Reagents for Organic Synthesis","author":"Mayr H."},{"key":"ref43\/cit43","volume-title":"Preparative Acetylenic Chemistry","author":"Brandsma L.","year":"1988","edition":"2"},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1016\/S0040-4039(00)81416-1","volume":"24","author":"Yamaguchi M.","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref45\/cit45a","first-page":"696","volume":"10","author":"Boeckman R. K.","year":"2004","journal-title":"Org. Synth. Coll."},{"key":"ref45\/cit45b","doi-asserted-by":"crossref","first-page":"2899","DOI":"10.1021\/jo00062a040","volume":"58","author":"Ireland R. E.","year":"1993","journal-title":"J. Org. Chem."},{"key":"ref46\/cit46","first-page":"310","volume":"5","author":"Eisenbraun E. J.","year":"1973","journal-title":"Org. Synth. Coll."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"4435","DOI":"10.1021\/ja00993a034","volume":"89","author":"Padwa A.","year":"1967","journal-title":"J. Am. Chem. Soc."},{"key":"ref48\/cit48","unstructured":"Due to the ready formation of allene the ketone1gwas not purified and was used as crude material for the reaction."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"199","DOI":"10.15227\/orgsyn.084.0199","volume":"84","author":"Sniady A.","year":"2007","journal-title":"Org. Synth."},{"key":"ref50\/cit50a","doi-asserted-by":"crossref","unstructured":"aKrause, N.; Hashmi, A. S. K.Modern Allene Chemistry,Wiley:Weinheim, 2004; pp3\u221250","DOI":"10.1002\/9783527619573"},{"key":"ref50\/cit50b","doi-asserted-by":"crossref","first-page":"342","DOI":"10.1002\/(SICI)1521-3897(199905)341:4<342::AID-PRAC342>3.0.CO;2-P","volume":"341","author":"Hashmi A. S. K.","year":"1999","journal-title":"J. Prakt. Chem."},{"key":"ref50\/cit50c","doi-asserted-by":"crossref","first-page":"7295","DOI":"10.1021\/jo970837l","volume":"62","author":"Hashmi A. S. K.","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1055\/s-2002-19771","author":"Schmieder-van de Vondervoort L.","year":"2002","journal-title":"Synlett"},{"key":"ref52\/cit52","unstructured":"Oxidation of alk-3-yn-1-ols to alk-3-yn-1-ones with the use of Dess\u2212Martin periodinane has been mentioned in ref32, but no preparative protocol was reported. For a workup leading mainly to alka-2,3-dien-1-ones see, for example, ref12a."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"1389","DOI":"10.1081\/SCC-100104049","volume":"31","author":"Ali M. H.","year":"2001","journal-title":"Synth. Commun."},{"key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"679","DOI":"10.1039\/a706779h","author":"Alvarez-Ibarra C.","year":"1998","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"2253","DOI":"10.1021\/ja01149a097","volume":"73","author":"King S. M.","year":"1951","journal-title":"J. Am. Chem. Soc."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"1948","DOI":"10.1021\/om800070j","volume":"27","author":"Greco J. F.","year":"2008","journal-title":"Organometallics"},{"key":"ref57\/cit57","unstructured":"SeeSupporting Information."},{"key":"ref58\/cit58","unstructured":"k= (0.191 \u00b1 0.007) M\u22121s\u22121."},{"key":"ref59\/cit59","unstructured":"Flash vacuum thermolysis reactions of allenyl ketones are known:"},{"key":"ref59\/cit59a","doi-asserted-by":"crossref","first-page":"1413","DOI":"10.1016\/0040-4020(82)80222-6","volume":"38","author":"Jullien J.","year":"1982","journal-title":"Tetrahedron"},{"key":"ref59\/cit59b","doi-asserted-by":"crossref","first-page":"3813","DOI":"10.1021\/jo00169a043","volume":"48","author":"Huntsman W. D.","year":"1983","journal-title":"J. Org. Chem."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1007\/s007830050045","volume":"1","author":"Kappe T.","year":"1996","journal-title":"Molecules"},{"key":"ref61\/cit61a","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.antiviral.2006.04.001","volume":"71","author":"McGuigan C.","year":"2006","journal-title":"Antiviral Res."},{"key":"ref61\/cit61b","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1002\/med.10035","volume":"23","author":"De Clercq E. D.","year":"2003","journal-title":"Med. Res. Rev."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"1854","DOI":"10.1021\/jo00159a012","volume":"48","author":"Robins M. J.","year":"1983","journal-title":"J. Org. Chem."},{"key":"ref63\/cit63","doi-asserted-by":"crossref","first-page":"3082","DOI":"10.1016\/j.bmc.2007.01.048","volume":"15","author":"Meneni S.","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref64\/cit64","doi-asserted-by":"crossref","first-page":"4993","DOI":"10.1021\/jm000210m","volume":"43","author":"McGuigan C.","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref65\/cit65a","doi-asserted-by":"crossref","first-page":"1239","DOI":"10.1016\/j.bmc.2004.11.057","volume":"13","author":"Amblard F.","year":"2005","journal-title":"Bioorg. Med. Chem."},{"key":"ref65\/cit65b","first-page":"2406","author":"Aucagne V.","year":"2006","journal-title":"Synlett"},{"key":"ref66\/cit66","doi-asserted-by":"crossref","first-page":"2997","DOI":"10.1055\/s-2006-948176","author":"Hudson R. H. E.","year":"2006","journal-title":"Synlett"},{"key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1039\/b109501c","author":"Esho N.","year":"2002","journal-title":"Chem. Commun."},{"key":"ref68\/cit68","doi-asserted-by":"crossref","first-page":"2711","DOI":"10.1039\/b605066b","author":"Ohshima T.","year":"2006","journal-title":"Chem. Commun."},{"key":"ref69\/cit69","doi-asserted-by":"crossref","first-page":"5147","DOI":"10.1021\/jo800625v","volume":"73","author":"Iwasaki T.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref70\/cit70","doi-asserted-by":"crossref","first-page":"2944","DOI":"10.1021\/ja711349r","volume":"130","author":"Ohshima T.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref71\/cit71","unstructured":"See for example:"},{"key":"ref71\/cit71a","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1139\/v71-076","volume":"49","author":"Neilson T.","year":"1971","journal-title":"Can. J. Chem."},{"key":"ref72\/cit72a","doi-asserted-by":"crossref","first-page":"2470","DOI":"10.1093\/nar\/24.13.2470","volume":"24","author":"Woo J.","year":"1996","journal-title":"Nucleic Acids Res."},{"key":"ref72\/cit72b","doi-asserted-by":"crossref","first-page":"870","DOI":"10.1055\/s-2007-973869","author":"Hudson R. H. E.","year":"2007","journal-title":"Synlett"},{"key":"ref73\/cit73","unstructured":"MeONa can be used for deacylation of furanopyrimidines in solution.(65b)"},{"key":"ref74\/cit74a","doi-asserted-by":"crossref","first-page":"1539","DOI":"10.1093\/nar\/gkh307","volume":"32","author":"Dash C.","year":"2004","journal-title":"Nucleic Acids Res."},{"key":"ref74\/cit74b","doi-asserted-by":"crossref","first-page":"2725","DOI":"10.1074\/jbc.M108856200","volume":"277","author":"Liu C.","year":"2002","journal-title":"J. Biol. Chem."},{"key":"ref75\/cit75a","doi-asserted-by":"crossref","first-page":"465","DOI":"10.1006\/jmbi.2001.4601","volume":"308","author":"Liu C.","year":"2001","journal-title":"J. Mol. Biol."},{"key":"ref75\/cit75b","doi-asserted-by":"crossref","first-page":"2555","DOI":"10.1039\/b502325d","author":"Ranasinghe R. T.","year":"2005","journal-title":"Chem. Commun."},{"key":"ref76\/cit76","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1016\/j.bmc.2004.11.013","volume":"13","author":"Esho N.","year":"2005","journal-title":"Bioorg. Med. Chem."},{"key":"ref77\/cit77","unstructured":"For deacetylation at 0 \u00b0C see:"},{"key":"ref77\/cit77a","doi-asserted-by":"crossref","first-page":"3897","DOI":"10.1021\/jm070210n","volume":"50","author":"Robins M. J.","year":"2007","journal-title":"J. Med. Chem."},{"key":"ref78\/cit78","unstructured":"Crystallographic data (excluding structural factors) for the structure reported in this paper were also deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-683563. These data can be obtained free of charge viawww.ccdc.cam.ac.uk\/data_request\/cif, by e-mailingdata_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223\u2212336033."},{"key":"ref79\/cit79","doi-asserted-by":"crossref","first-page":"953","DOI":"10.1021\/ol062933r","volume":"9","author":"Donohoe T. J.","year":"2007","journal-title":"Org. Lett."},{"key":"ref80\/cit80","unstructured":"Freshly prepared Dess\u2212Martin periodinane reagent was used at 1.2 equiv stoichiometry. Prolonged storage of the reagent required the use of additional amounts, up to 1.5 equiv."},{"key":"ref81\/cit81","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1246\/bcsj.71.475","volume":"71","author":"Koga Y.","year":"1998","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref82\/cit82","unstructured":"The1H and13C NMR chemical shifts are in ppm, andJvalues are in Hz."},{"key":"ref83\/cit83","unstructured":"Thei\/o\/m\/ppositions were designated with respect to the pyrimidine group."},{"key":"ref84\/cit84","doi-asserted-by":"crossref","first-page":"7012","DOI":"10.1021\/jm058167w","volume":"48","author":"Rai D.","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref85\/cit85","unstructured":"Multiplicity was not determined in the13C NMR spectrum (peaks were obscured)."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo8007995","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,15]],"date-time":"2023-03-15T08:15:41Z","timestamp":1678868141000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo8007995"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,7,3]]},"references-count":151,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2008,8,1]]}},"alternative-id":["10.1021\/jo8007995"],"URL":"https:\/\/doi.org\/10.1021\/jo8007995","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,7,3]]}}}