{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,12]],"date-time":"2026-03-12T05:17:23Z","timestamp":1773292643495,"version":"3.50.1"},"reference-count":47,"publisher":"Wiley","issue":"49","license":[{"start":{"date-parts":[[2022,11,10]],"date-time":"2022-11-10T00:00:00Z","timestamp":1668038400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21871161, 22171161"],"award-info":[{"award-number":["21871161, 22171161"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2022,12,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A direct spirocyclization approach for the chemical synthesis of spiro[cyclohexane\u20102\u2010indoline] alkaloids is reported. The absolute stereochemistry was introduced by a desymmetrizing Dieckmann condensation, and the relative stereochemistry was controlled by the manipulation of the kinetic and thermodynamic pathways of the spirocyclization. By contrast to the biogenetic proposal involving the diester\u2010type alkaloid as the precursor, we demonstrate that chemically a common lactone\u2010type intermediate could bridge the chemical synthesis of this class of natural products.<\/jats:p>","DOI":"10.1002\/anie.202212042","type":"journal-article","created":{"date-parts":[[2022,10,13]],"date-time":"2022-10-13T02:24:25Z","timestamp":1665627865000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Total Synthesis of Spiro[cyclohexane\u20102\u2010indoline] Alkaloids: A Regio\u2010 and Diastereoselective Spirocyclization Approach"],"prefix":"10.1002","volume":"61","author":[{"given":"Lu","family":"Chen","sequence":"first","affiliation":[{"name":"School of Pharmaceutical Sciences Key Laboratory of Bioorganic Phosphorus Chemistry &amp; Chemical Biology (Ministry of Education) Beijing Advanced Innovation Center for Structural Biology &amp; Frontier Research Center for Biological Structure Tsinghua University  Beijing 100084 China"},{"name":"Key Laboratory of Biopesticide and Chemical Biology (Ministry of education) College of Plant Protection Fujian Agriculture and Forestry University  Fuzhou Fujian 350002 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kejing","family":"Xie","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Key Laboratory of Bioorganic Phosphorus Chemistry &amp; Chemical Biology (Ministry of Education) Beijing Advanced Innovation Center for Structural Biology &amp; Frontier Research Center for Biological Structure Tsinghua University  Beijing 100084 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jingyang","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Key Laboratory of Bioorganic Phosphorus Chemistry &amp; Chemical Biology (Ministry of Education) Beijing Advanced Innovation Center for Structural Biology &amp; Frontier Research Center for Biological Structure Tsinghua University  Beijing 100084 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7747-2979","authenticated-orcid":false,"given":"Liansuo","family":"Zu","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Key Laboratory of Bioorganic Phosphorus Chemistry &amp; Chemical Biology (Ministry of Education) Beijing Advanced Innovation Center for Structural Biology &amp; Frontier Research Center for Biological Structure Tsinghua University  Beijing 100084 China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,11,10]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)92223-8"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/np50097a018"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.08.091"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/np200008g"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/bs.alkal.2017.01.001"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QO00786H"},{"key":"e_1_2_3_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0QO01165G"},{"key":"e_1_2_3_9_1","unstructured":"For the total synthesis of the lactone-type alkaloids see:"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016007d"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo048917u"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510561"},{"key":"e_1_2_3_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201510561"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201801312"},{"key":"e_1_2_3_14_1","unstructured":"For the total synthesis of the cyclopropane-type alkaloids see:"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4034786"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201400464"},{"key":"e_1_2_3_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201400464"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201403407"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409963"},{"key":"e_1_2_3_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201409963"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201502011"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01428"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00210"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803702"},{"key":"e_1_2_3_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201803702"},{"key":"e_1_2_3_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00591"},{"key":"e_1_2_3_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b13484"},{"key":"e_1_2_3_25_1","unstructured":"For examples of 5-exo addition:"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc10999e"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401538b"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03428"},{"key":"e_1_2_3_29_1","unstructured":"For examples of 6-endo addition:"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308127"},{"key":"e_1_2_3_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201308127"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201300920"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01654"},{"key":"e_1_2_3_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.08.054"},{"key":"e_1_2_3_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol049074w"},{"key":"e_1_2_3_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00094"},{"key":"e_1_2_3_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00260a040"},{"key":"e_1_2_3_37_1","unstructured":"UsingL-menthol as the directing group failed to produce15."},{"key":"e_1_2_3_38_1","unstructured":"Deposition number\u20052201434contains the supplementary crystallographic data for this paper. 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