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Soc."},{"key":"ref9\/cit9c","doi-asserted-by":"publisher","DOI":"10.1021\/jo034989u"},{"key":"ref10\/cit10a","doi-asserted-by":"publisher","DOI":"10.1021\/jo00399a052"},{"key":"ref10\/cit10b","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00306-W"},{"key":"ref11\/cit11a","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020315)41:6<996::AID-ANIE996>3.0.CO;2-I"},{"key":"ref11\/cit11b","doi-asserted-by":"publisher","DOI":"10.1021\/ja012127+"},{"key":"ref12\/cit12a","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505034"},{"key":"ref12\/cit12b","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100926"},{"key":"ref12\/cit12c","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11872"},{"key":"ref13\/cit13a","doi-asserted-by":"publisher","DOI":"10.1021\/ja044812x"},{"key":"ref13\/cit13b","doi-asserted-by":"publisher","DOI":"10.1021\/ja710294k"},{"key":"ref14\/cit14","unstructured":"The\ndifficulties encountered\nin its preparation explain why to date ketone 1 is not\nbroadly employed in synthesis despite its apparent potential as a\nbuilding block."},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)93853-X"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.1021\/ja01533a023"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)89494-0"},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1021\/ja00029a036"},{"key":"ref19\/cit19a","doi-asserted-by":"publisher","DOI":"10.1021\/jo00219a039"},{"key":"ref19\/cit19b","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC05404K"},{"key":"ref19\/cit19c","doi-asserted-by":"publisher","DOI":"10.1021\/ol301513h"},{"key":"ref20\/cit20","unstructured":"The corresponding overall\nyield of 1 from the starting material of iodide 10 would be much lower. For instance, the overall yield from 11 would be only 5\u201315%."},{"key":"ref21\/cit21","unstructured":"With the corresponding\noverall yield of 1 from 11 being 9\u201328%."},{"key":"ref22\/cit22","unstructured":"Presumably is caused\nby the great tendency of methyl vinyl ketone (MVK) to polymerize.\nAnother problem associated with MVK is the accessibility: In China,\nMVK is a strictly regulated substance, which is practically impossible\nto purchase and definitely not permitted to store in ordinary laboratories."},{"key":"ref23\/cit23a","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob26642c"},{"key":"ref23\/cit23b","doi-asserted-by":"publisher","DOI":"10.1071\/CH07253"},{"key":"ref23\/cit23c","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800089"},{"key":"ref24\/cit24","unstructured":"Further acidification\nled to hydrolysis of substantial amounts of 15 back to 14."},{"key":"ref25\/cit25","unstructured":"As compound 15 has never been reported\nbefore, for complete documentation, its\nphysical and spectroscopic data are also collected on a small purified\nsample."},{"key":"ref26\/cit26","unstructured":"For safety reasons,\nin our institute. performing hydrogenation in ordinary laboratories\nis prohibited; such experiments must be carried out in a special laboratory\nshared by the whole institute, and booking a space there prior to\nevery use is required."},{"key":"ref27\/cit27a","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)00636-5"},{"key":"ref27\/cit27b","doi-asserted-by":"publisher","DOI":"10.3184\/030823409X393637"},{"key":"ref28\/cit28a","doi-asserted-by":"publisher","DOI":"10.24820\/ark.5550190.p010.277"},{"key":"ref28\/cit28b","doi-asserted-by":"publisher","DOI":"10.33224\/rrch.2020.65.1.05"},{"key":"ref29\/cit29a","doi-asserted-by":"publisher","DOI":"10.1016\/j.crci.2013.09.013"},{"key":"ref29\/cit29b","doi-asserted-by":"publisher","DOI":"10.1016\/j.crci.2014.10.011"},{"key":"ref30\/cit30","unstructured":"There\nhave been a large\nnumber of reports on the Al-Ni alloy based reduction of phenyl rings\nin water, but to date, almost all the studies are methodological rather\nthan synthetic in nature, involving only simple monofunctional substrates.\nPerhaps this is why such a nice inexpensive\/practical reduction method\nappears to be largely overlooked by the synthetic community."},{"key":"ref31\/cit31","unstructured":"Oxidation\nof a mixture\nof these side products (free from any methyl ketone 17 as shown by the 1H NMR) with NaClO\/TEMPO\/KBr gave the\nknown dione 18 in 72% yield as the only observed product,\nindicating that the starting material must consist mainly of the diastereomers\nof diol 16. Note that before the C-3\u2032 must have\nbeen reduced by Al-Ni alloy\/aq. KOH at 90 \u00b0C, the ketal function\nwas hydrolyzed to a free ketone under strongly basic conditions, an\nevent somewhat unexpected and thus worthy of mentioning."},{"key":"ref32\/cit32a","doi-asserted-by":"crossref","first-page":"7321","DOI":"10.1039\/c2ob25941a","volume":"10","author":"Tomin A.","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"ref32\/cit32b","doi-asserted-by":"publisher","DOI":"10.2174\/157017811799304115"},{"key":"ref33\/cit33","doi-asserted-by":"publisher","DOI":"10.1021\/jo00388a038"},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"5621","DOI":"10.1021\/jo00234a021","volume":"52","author":"Taber D. F.","year":"1987","journal-title":"J. Org. Chem."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"2430","DOI":"10.1002\/adsc.201300439","volume":"355","author":"Li N.","year":"2013","journal-title":"Adv. Synth. Catal."},{"key":"ref36\/cit36","unstructured":"The crude product was\nrather pure, with 1H and 13C NMR essentially\nthe same as those recorded after removal of the colored species by\nfiltration through silica gel."},{"key":"ref37\/cit37","unstructured":"Without this route,\nit would have been impossible for us to get enough quantity of ketone 1 for the total synthesis of panamonon B (ref 1c)."},{"key":"ref38\/cit38","unstructured":"It\nis possible to use\na magnetic stirrer in sub-gram-scale experiments, though some of the\nAl\u2013Ni and the Ra-Ni formed during the reaction might stick\nto the stirring bar. However, for larger-scale experiments, a mechanical\nstirrer proved necessary for effective suspension of the solids in\nthe reaction mixture."},{"key":"ref39\/cit39","unstructured":"CAS [7681-52-9]."},{"key":"ref40\/cit40","unstructured":"It was not possible\nto use pH test paper here because of the bleaching effect of NaClO;\na pH-meter was used."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.1c05159","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.1c05159","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,15]],"date-time":"2023-04-15T11:20:46Z","timestamp":1681557646000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acsomega.1c05159"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,2]]},"references-count":65,"journal-issue":{"issue":"45","published-print":{"date-parts":[[2021,11,16]]}},"alternative-id":["10.1021\/acsomega.1c05159"],"URL":"https:\/\/doi.org\/10.1021\/acsomega.1c05159","relation":{},"ISSN":["2470-1343","2470-1343"],"issn-type":[{"value":"2470-1343","type":"print"},{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,2]]}}}