{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T06:01:24Z","timestamp":1760853684090,"version":"build-2065373602"},"reference-count":154,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2013,6,20]],"date-time":"2013-06-20T00:00:00Z","timestamp":1371686400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2013,8,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Herein, we describe the first asymmetric total synthesis and determination of the relative and absolute stereochemistry of naturally occurring 16\u2010hydroxy\u201016,22\u2010dihydroapparicine. The key steps include 1)\u2005a novel phosphinimine\u2010mediated cascade reaction to construct the unique 1\u2010azabicyclo[4.2.2]decane core, including a pseudo\u2010aminal\u2010type moiety; 2)\u2005a highly stereospecific 1,2\u2010addition of 2\u2010acylindole or a methylketone through a Felkin\u2013Anh transition state for the construction of a tetrasubstituted carbon center; and 3)\u2005an intramolecular chirality\u2010transferring Michael reaction of the ketoester, with neighboring\u2010group participation, to introduce a chiral center at C15 in the target molecule. In addition, we evaluated the antimalarial activity of synthetic (+)\u2010(15<jats:italic>S<\/jats:italic>,16<jats:italic>R<\/jats:italic>)\u201016\u2010hydroxy\u201016,22\u2010dihydroapparicine and its intermediate against chloroquine\u2010resistant <jats:italic>Plasmodium falciparum<\/jats:italic> (K1 strain) parasites.<\/jats:p>","DOI":"10.1002\/chem.201300292","type":"journal-article","created":{"date-parts":[[2013,6,20]],"date-time":"2013-06-20T12:01:13Z","timestamp":1371729673000},"page":"10741-10750","source":"Crossref","is-referenced-by-count":13,"title":["Structure Determination and Total Synthesis of (+)\u201016\u2010Hydroxy\u201016,22\u2010dihydroapparicine"],"prefix":"10.1002","volume":"19","author":[{"given":"Tomoyasu","family":"Hirose","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshihiko","family":"Noguchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yujiro","family":"Furuya","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aki","family":"Ishiyama","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masato","family":"Iwatsuki","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuhiko","family":"Otoguro","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Satoshi","family":"\u014cmura","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Toshiaki","family":"Sunazuka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2013,6,20]]},"reference":[{"key":"e_1_2_5_1_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.2042-7158.1970.tb08441.x"},{"key":"e_1_2_5_2_2","unstructured":"\u00a0"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(65)80057-6"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9650004773"},{"key":"e_1_2_5_5_2","unstructured":"\u00a0"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19640470750"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)95164-0"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.3987\/R-1985-12-2975"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50045a012"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00269256"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50052a023"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(90)80208-X"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2005.02.018"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2011.08.001"},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50035a014"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol102709s"},{"key":"e_1_2_5_17_2","unstructured":"\u00a0"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo981723s"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo990147c"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo062184r"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01349-0"},{"key":"e_1_2_5_22_2","unstructured":"\u00a0"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.3987\/R-1981-06-0941"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0013406"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050484"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604377"},{"key":"e_1_2_5_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604377"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070259i"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.11.068"},{"key":"e_1_2_5_29_2","unstructured":"\u00a0"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0030820"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol063042m"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol017310m"},{"key":"e_1_2_5_33_2","unstructured":"\u00a0"},{"key":"e_1_2_5_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0162320"},{"key":"e_1_2_5_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol8008655"},{"key":"e_1_2_5_36_2","unstructured":"\u00a0"},{"key":"e_1_2_5_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00626-2"},{"key":"e_1_2_5_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.12.016"},{"key":"e_1_2_5_39_2","unstructured":"\u00a0"},{"key":"e_1_2_5_40_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-969666"},{"key":"e_1_2_5_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50039a008"},{"key":"e_1_2_5_42_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-969101"},{"key":"e_1_2_5_43_2","doi-asserted-by":"publisher","DOI":"10.1211\/0022357991777092"},{"key":"e_1_2_5_44_2","unstructured":"\u00a0"},{"key":"e_1_2_5_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/b903577j"},{"key":"e_1_2_5_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo901986v"},{"key":"e_1_2_5_47_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1050"},{"key":"e_1_2_5_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.01.110"},{"key":"e_1_2_5_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01037a052"},{"key":"e_1_2_5_50_2","unstructured":"\u00a0"},{"key":"e_1_2_5_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00833a085"},{"key":"e_1_2_5_52_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1980-28997"},{"key":"e_1_2_5_53_2","doi-asserted-by":"publisher","DOI":"10.1080\/00304949509458177"},{"key":"e_1_2_5_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200390139"},{"key":"e_1_2_5_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01316-1"},{"key":"e_1_2_5_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00304a019"},{"key":"e_1_2_5_57_2","unstructured":"\u00a0"},{"key":"e_1_2_5_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00475a040"},{"key":"e_1_2_5_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39780000601"},{"key":"e_1_2_5_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00002-2"},{"key":"e_1_2_5_61_2","unstructured":"\u00a0"},{"key":"e_1_2_5_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00175a043"},{"key":"e_1_2_5_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo962187b"},{"key":"e_1_2_5_64_2","first-page":"87","volume":"37","author":"Fukuyama T.","year":"2004","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_5_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8022169"},{"key":"e_1_2_5_66_2","unstructured":"\u00a0"},{"key":"e_1_2_5_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00033a029"},{"key":"e_1_2_5_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja201254c"},{"key":"e_1_2_5_69_2","unstructured":"\u00a0"},{"key":"e_1_2_5_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_5_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol017273z"},{"key":"e_1_2_5_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502008"},{"key":"e_1_2_5_72_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502008"},{"key":"e_1_2_5_73_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.41.854"},{"key":"e_1_2_5_74_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)10653-0"},{"key":"e_1_2_5_75_2","unstructured":"\u00a0"},{"key":"e_1_2_5_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00338a050"},{"key":"e_1_2_5_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00135a035"},{"key":"e_1_2_5_78_2","unstructured":"\u00a0"},{"key":"e_1_2_5_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00350a104"},{"key":"e_1_2_5_80_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(00)80331-5"},{"key":"e_1_2_5_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.05.112"},{"key":"e_1_2_5_82_2","unstructured":"\u00a0"},{"key":"e_1_2_5_83_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01279-4"},{"key":"e_1_2_5_84_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01280-0"},{"key":"e_1_2_5_85_2","unstructured":"\u00a0"},{"key":"e_1_2_5_86_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)81663-X"},{"key":"e_1_2_5_87_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2001.424"},{"key":"e_1_2_5_88_2","unstructured":"\u00a0"},{"key":"e_1_2_5_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570220260"},{"key":"e_1_2_5_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00034a058"},{"key":"e_1_2_5_91_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)00696-2"},{"key":"e_1_2_5_92_2","unstructured":"\u00a0"},{"key":"e_1_2_5_93_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.42b-0384"},{"key":"e_1_2_5_94_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.43-0706"},{"key":"e_1_2_5_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1522-2675(19991006)82:10<1753::AID-HLCA1753>3.0.CO;2-Y"},{"key":"e_1_2_5_96_2","doi-asserted-by":"publisher","DOI":"10.1002\/1522-2675(20011219)84:12<3773::AID-HLCA3773>3.0.CO;2-E"},{"key":"e_1_2_5_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol036179a"},{"key":"e_1_2_5_98_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkp815"},{"key":"e_1_2_5_99_2","unstructured":"\u00a0"},{"key":"e_1_2_5_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00959a018"},{"key":"e_1_2_5_101_2","first-page":"1","volume":"26","author":"Gschwend H. W.","year":"1979","journal-title":"Organomet. React."},{"key":"e_1_2_5_102_2","unstructured":"N\u2010TBSOM\u20102\u2010iodoindole37was prepared from commercially available 2\u2010iodoindole."},{"key":"e_1_2_5_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00136a008"},{"key":"e_1_2_5_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00098a009"},{"key":"e_1_2_5_105_2","unstructured":"\u00a0"},{"key":"e_1_2_5_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00148a023"},{"key":"e_1_2_5_107_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-99-S143"},{"key":"e_1_2_5_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0200421"},{"key":"e_1_2_5_109_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802021"},{"key":"e_1_2_5_110_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39760000734"},{"key":"e_1_2_5_111_2","unstructured":"\u00a0"},{"key":"e_1_2_5_112_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00196a065"},{"key":"e_1_2_5_113_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0014281"},{"key":"e_1_2_5_114_2","unstructured":"\u00a0"},{"key":"e_1_2_5_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo015756a"},{"key":"e_1_2_5_116_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.04.079"},{"key":"e_1_2_5_117_2","unstructured":"\u00a0"},{"key":"e_1_2_5_118_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19580910113"},{"key":"e_1_2_5_119_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80205-7"},{"key":"e_1_2_5_120_2","unstructured":"\u00a0"},{"key":"e_1_2_5_121_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00025a043"},{"key":"e_1_2_5_122_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja046824o"},{"key":"e_1_2_5_123_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00011a031"},{"key":"e_1_2_5_124_2","unstructured":"\u00a0"},{"key":"e_1_2_5_125_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)80411-6"},{"key":"e_1_2_5_126_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00268a013"},{"key":"e_1_2_5_127_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397919608004591"},{"key":"e_1_2_5_128_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.11.006"},{"key":"e_1_2_5_129_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00371a006"},{"key":"e_1_2_5_130_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800480d"},{"key":"e_1_2_5_131_2","unstructured":"\u00a0"},{"key":"e_1_2_5_132_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00221a012"},{"key":"e_1_2_5_133_2","doi-asserted-by":"publisher","DOI":"10.1039\/b305881f"},{"key":"e_1_2_5_134_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061320b"},{"key":"e_1_2_5_135_2","unstructured":"TheS\u2005configuration of the C3 center of (\u2212)\u201052was determined after hydrogenation."},{"key":"e_1_2_5_136_2","unstructured":"\u00a0"},{"key":"e_1_2_5_137_2","doi-asserted-by":"publisher","DOI":"10.1039\/b603570a"},{"key":"e_1_2_5_138_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo801108h"},{"key":"e_1_2_5_139_2","unstructured":"\u00a0"},{"key":"e_1_2_5_140_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60304a005"},{"key":"e_1_2_5_141_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol026145n"},{"key":"e_1_2_5_142_2","unstructured":"\u00a0"},{"key":"e_1_2_5_143_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9606440"},{"key":"e_1_2_5_144_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja074300t"},{"key":"e_1_2_5_145_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo8005599"},{"key":"e_1_2_5_146_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol102795g"},{"key":"e_1_2_5_147_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1193225"},{"key":"e_1_2_5_148_2","unstructured":"\u00a0"},{"key":"e_1_2_5_149_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.54.658"},{"key":"e_1_2_5_150_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.55.832"},{"key":"e_1_2_5_151_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2010.124"},{"key":"e_1_2_5_152_2","doi-asserted-by":"crossref","unstructured":"S. R.Meshnick M. J.Dobson \u201cThe history of antimalarial drugs\u201d inAntimalarial chemotherapy: mechanisms of action resistance and new directions in drug discovery(Ed: P.\u2005J. Rosenthal) Humana Press Totowa 15\u201325 2001.","DOI":"10.1007\/978-1-59259-111-4_2"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201300292","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201300292","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T21:50:28Z","timestamp":1760305828000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201300292"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,6,20]]},"references-count":154,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2013,8,5]]}},"alternative-id":["10.1002\/chem.201300292"],"URL":"https:\/\/doi.org\/10.1002\/chem.201300292","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2013,6,20]]}}}