{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,9,23]],"date-time":"2025-09-23T14:08:02Z","timestamp":1758636482305},"reference-count":35,"publisher":"Pharmaceutical Society of Japan","issue":"1","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem. Pharm. Bull.","CHEMICAL &amp; PHARMACEUTICAL BULLETIN"],"published-print":{"date-parts":[[2022,1,1]]},"DOI":"10.1248\/cpb.c21-00837","type":"journal-article","created":{"date-parts":[[2021,11,1]],"date-time":"2021-11-01T22:08:24Z","timestamp":1635804504000},"page":"89-93","source":"Crossref","is-referenced-by-count":3,"title":["A Stereoselective Synthesis of Fused Carbocycles with a &lt;i&gt;cis&lt;\/i&gt;-1,2-Diol Moiety by Desymmetrization: SmI&lt;sub&gt;2&lt;\/sub&gt;-Mediated Pinacol Coupling of &lt;i&gt;meso&lt;\/i&gt;-Cyclic 1,3-Diones"],"prefix":"10.1248","volume":"70","author":[{"given":"Keita","family":"Komine","sequence":"first","affiliation":[{"name":"Graduate School of Biomedical Sciences, Nagasaki University"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Riki","family":"Ninomiya","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical Sciences, Nagasaki University"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hayato","family":"Fukuda","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical Sciences, Nagasaki University"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jun","family":"Ishihara","sequence":"additional","affiliation":[{"name":"Graduate School of Biomedical Sciences, Nagasaki University"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"163","reference":[{"key":"1","doi-asserted-by":"crossref","unstructured":"1) Linn T. Z., Awale S., Tezuka Y., Banskota A. H., Kalauni S. K., Attamimi F., Ueda J., Asih P. B. S., Syafruddin D., Tanaka K., Kadota S., <i>J. Nat. Prod.<\/i>, <b>68<\/b>, 706\u2013710 (2005).","DOI":"10.1021\/np0401720"},{"key":"2","doi-asserted-by":"crossref","unstructured":"2) Chen J.-J., Li Z.-M., Gao K., Chang J., Yao X.-J., <i>J. Nat. Prod.<\/i>, <b>72<\/b>, 1128\u20131132 (2009).","DOI":"10.1021\/np900120q"},{"key":"3","doi-asserted-by":"crossref","unstructured":"3) Wang S.-K., Lee Y.-S., Duh C.-Y., <i>Mar. Drugs<\/i>, <b>10<\/b>, 1528\u20131535 (2012).","DOI":"10.3390\/md10071528"},{"key":"4","doi-asserted-by":"crossref","unstructured":"4) Corey E. J., <i>Angew. Chem. Int. Ed.<\/i>, <b>41<\/b>, 1650\u20131667 (2002).","DOI":"10.1002\/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO;2-B"},{"key":"5","doi-asserted-by":"crossref","unstructured":"5) Nicolaou K. C., Snyder S. A., Montagnon T., Vassilikogiannakis G., <i>Angew. Chem. Int. Ed.<\/i>, <b>41<\/b>, 1668\u20131698 (2002).","DOI":"10.1002\/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z"},{"key":"6","doi-asserted-by":"crossref","unstructured":"6) Peng F., Dai M., Angeles A. R., Danishefsky S., <i>J. Chem. Sci.<\/i>, <b>3<\/b>, 3076\u20133080 (2012).","DOI":"10.1039\/c2sc20868g"},{"key":"7","doi-asserted-by":"crossref","unstructured":"7) Oppolzer W., \u201cComprehensive Organic Synthesis,\u201d Vol. 5, Chap. 4. 1, ed. by Trost B. M., Fleming I., Pergamon Press, Oxford, 1991, pp. 315\u2013399.","DOI":"10.1016\/B978-0-08-052349-1.00128-1"},{"key":"8","doi-asserted-by":"crossref","unstructured":"8) List B., <i>Tetrahedron<\/i>, <b>58<\/b>, 5573\u20135590 (2002).","DOI":"10.1016\/S0040-4020(02)00516-1"},{"key":"9","doi-asserted-by":"crossref","unstructured":"9) Allemann C., Gordillo R., Clemente F. R., Cheong P. H.-Y., Houk K. N., <i>Acc. Chem. Res.<\/i>, <b>37<\/b>, 558\u2013569 (2004).","DOI":"10.1021\/ar0300524"},{"key":"10","doi-asserted-by":"crossref","unstructured":"10) Heathcock C. H., \u201cComprehensive Organic Synthesis,\u201d Vol. 2, Chap. 1. 5, ed. by Trost B. M., Fleming I., Pergamon Press, Oxford, 1991, pp. 133\u2013179.","DOI":"10.1016\/B978-0-08-052349-1.00027-5"},{"key":"11","doi-asserted-by":"crossref","unstructured":"11) Hajos Z. G., Parrish D. R., <i>J. Org. Chem.<\/i>, <b>39<\/b>, 1615\u20131621 (1974).","DOI":"10.1021\/jo00925a003"},{"key":"12","doi-asserted-by":"crossref","unstructured":"12) Eder U., Sauer G., Wiechert R., <i>Angew. Chem. Int. Ed. Engl.<\/i>, <b>10<\/b>, 496\u2013497 (1971).","DOI":"10.1002\/anie.197104961"},{"key":"13","doi-asserted-by":"crossref","unstructured":"13) Bradshaw B., Bonjoch J., <i>Synlett<\/i>, <b>2012<\/b>, 337\u2013356 (2012).","DOI":"10.1055\/s-0031-1290107"},{"key":"14","doi-asserted-by":"crossref","unstructured":"14) Komine K., Urayama Y., Hosaka T., Fukuda H., Hatakeyama S., Ishihara J., <i>Chirality<\/i>, <b>32<\/b>, 273\u2013281 (2020).","DOI":"10.1002\/chir.23173"},{"key":"15","doi-asserted-by":"crossref","unstructured":"15) Suzuki K., Tamiya M., \u201cPinacol Coupling Reactions: Comprehensive Organic Synthesis,\u201d 2nd ed., Vol. III. Chap. 11, ed. by Knochel P., Molander G. A., Elsevier, Amsterdam, 2014, pp. 580\u2013620.","DOI":"10.1016\/B978-0-08-097742-3.00316-5"},{"key":"16","doi-asserted-by":"crossref","unstructured":"16) Chatterjee A., Joshi N. N., <i>Tetrahedron<\/i>, <b>62<\/b>, 12137\u201312158 (2006).","DOI":"10.1016\/j.tet.2006.09.002"},{"key":"17","doi-asserted-by":"crossref","unstructured":"17) Namy J. L., Souppe J., Kagan H. B., <i>Tetrahedron Lett.<\/i>, <b>24<\/b>, 765\u2013766 (1983).","DOI":"10.1016\/S0040-4039(00)81521-X"},{"key":"18","doi-asserted-by":"crossref","unstructured":"18) Molander G. A., Kenny C., <i>J. Org. Chem.<\/i>, <b>53<\/b>, 2132\u20132134 (1988).","DOI":"10.1021\/jo00244a062"},{"key":"19","doi-asserted-by":"crossref","unstructured":"19) Molander G. A., Kenny C., <i>J. Am. Chem. Soc.<\/i>, <b>111<\/b>, 8236\u20138246 (1989).","DOI":"10.1021\/ja00203a027"},{"key":"20","doi-asserted-by":"crossref","unstructured":"20) Chiara J. L., Cabri W., Hanessian S., <i>Tetrahedron Lett.<\/i>, <b>32<\/b>, 1125\u20131128 (1991).","DOI":"10.1016\/S0040-4039(00)92024-0"},{"key":"21","doi-asserted-by":"crossref","unstructured":"21) Uenishi J., Masuda S., Wakabayashi S., <i>Tetrahedron Lett.<\/i>, <b>32<\/b>, 5097\u20135100 (1991).","DOI":"10.1016\/S0040-4039(00)93437-3"},{"key":"22","doi-asserted-by":"crossref","unstructured":"22) Chiara J. L., Martin-Lomas M., <i>Tetrahedron Lett.<\/i>, <b>35<\/b>, 2969\u20132972 (1994).","DOI":"10.1016\/S0040-4039(00)76674-3"},{"key":"23","doi-asserted-by":"crossref","unstructured":"23) Molander G. A., Harris C. R., <i>Chem. Rev.<\/i>, <b>96<\/b>, 307\u2013338 (1996).","DOI":"10.1021\/cr950019y"},{"key":"24","unstructured":"24) Procter D. J., Flowers R. A. II, Skrydstrup T., \u201cOrganic Synthesis Using Samarium Diiodide: A Practical Guide,\u201d RSC Publishing, Cambridge, 2010."},{"key":"25","doi-asserted-by":"crossref","unstructured":"25) Szostak M., Fazakerley N. J., Parmar D., Procter D. J., <i>Chem. Rev.<\/i>, <b>114<\/b>, 5959\u20136039 (2014).","DOI":"10.1021\/cr400685r"},{"key":"26","doi-asserted-by":"crossref","unstructured":"26) Nicolaou K. C., Ding H., Richard J.-A., Chen D. Y.-K., <i>J. Am. Chem. Soc.<\/i>, <b>132<\/b>, 3815\u20133818 (2010).","DOI":"10.1021\/ja9093988"},{"key":"27","doi-asserted-by":"crossref","unstructured":"27) Sasano Y., Koyama J., Yoshikawa K., Kanoh N., Kwon E., Iwabuchi Y., <i>Org. Lett.<\/i>, <b>20<\/b>, 3053\u20133056 (2018).","DOI":"10.1021\/acs.orglett.8b01087"},{"key":"28","doi-asserted-by":"crossref","unstructured":"28) Zhang Y.-A., Milkovits A., Agarawal V., Taylor C. A., Snyder S. A., <i>Angew. Chem. Int. Ed.<\/i>, <b>60<\/b>, 11127\u201311132 (2021).","DOI":"10.1002\/anie.202016178"},{"key":"29","doi-asserted-by":"crossref","unstructured":"29) Edmonds D. J., Johnston D., Procter D. J., <i>Chem. Rev.<\/i>, <b>104<\/b>, 3371\u20133404 (2004).","DOI":"10.1021\/cr030017a"},{"key":"30","doi-asserted-by":"crossref","unstructured":"30) Nicolaou K. C., Ellery S. P., Chen J. S., <i>Angew. Chem. Int. Ed.<\/i>, <b>48<\/b>, 7140\u20137165 (2009).","DOI":"10.1002\/anie.200902151"},{"key":"31","doi-asserted-by":"crossref","unstructured":"31) Only relevant example is Sugai\u2019s work which involves a pinacol coupling of the cyclic ketol, derived from cyclic 1,3-dione by enzymatic desymmetrization.; Fujieda S., Tomita M., Fuhshuku K., Ohba S., Nishiyama S., Sugai T., <i>Adv. Synth. Catal.<\/i>, <b>347<\/b>, 1099\u20131109 (2005).","DOI":"10.1002\/adsc.200505034"},{"key":"32","unstructured":"32) These data can be obtained free of charge <i>via<\/i> www.ccdc.cam.ac.uk\/data_request\/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033."},{"key":"33","doi-asserted-by":"crossref","unstructured":"33) Aspinall H. C., Greeves N., Valla C., <i>Org. Lett.<\/i>, <b>7<\/b>, 1919\u20131922 (2005).","DOI":"10.1021\/ol050256f"},{"key":"34","doi-asserted-by":"crossref","unstructured":"34) Kawatsura M., Kishi E., Kito M., Sakai T., Shirahama H., Matsuda F., <i>Synlett<\/i>, <b>1997<\/b> (Sup. I), 479\u2013480 (1997).","DOI":"10.1055\/s-1997-6153"},{"key":"35","doi-asserted-by":"crossref","unstructured":"35) Komine K., Lambert K. M., Savage Q. R., Cox J. B., Wood J. L., <i>Chem. Sci.<\/i>, <b>11<\/b>, 9488\u20139493 (2020).","DOI":"10.1039\/D0SC03422C"}],"container-title":["Chemical and Pharmaceutical Bulletin"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/70\/1\/70_c21-00837\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T03:43:39Z","timestamp":1641008619000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/70\/1\/70_c21-00837\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,1]]},"references-count":35,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2022]]}},"URL":"https:\/\/doi.org\/10.1248\/cpb.c21-00837","relation":{},"ISSN":["0009-2363","1347-5223"],"issn-type":[{"value":"0009-2363","type":"print"},{"value":"1347-5223","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,1,1]]},"article-number":"c21-00837"}}