uni-leipzig-open-access/json/anie.202302475

{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,1,20]],"date-time":"2024-01-20T07:24:42Z","timestamp":1705735482323},"reference-count":48,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2023,5,5]],"date-time":"2023-05-05T00:00:00Z","timestamp":1683244800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["SCHN 441\/11-2"]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2023,6,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report herein the catalytic asymmetric cyclization of 1\u2010aryl terpenols to afford enantiomerically highly enriched <jats:italic>\u0394<\/jats:italic><jats:sup>9<\/jats:sup>\u2010<jats:italic>cis<\/jats:italic>\u2010tetrahydrocannabinoid scaffolds in a single step. As powerful chiral catalysts strongly acidic imidodiphosphorimidates (IDPis) have been identified which furnish the products with good yields and excellent enantioselectivity. Upon MOM\u2010deprotection some naturally occurring cannabimimetica such as (\u2212)\u2010<jats:italic>cis<\/jats:italic>\u2010<jats:italic>\u0394<\/jats:italic><jats:sup>9<\/jats:sup>\u2010tetrahydrocannabinol and (\u2212)\u2010perrottetinene as well as some unnatural analogues were made accessible along a merely 3\u2010step biomimetic sequence (MOM=methoxymethyl).<\/jats:p>","DOI":"10.1002\/anie.202302475","type":"journal-article","created":{"date-parts":[[2023,4,14]],"date-time":"2023-04-14T10:59:31Z","timestamp":1681469971000},"update-policy":"http:\/\/dx.doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Br\u00f8nsted Acid Catalyzed Asymmetric Synthesis of <i>cis<\/i>\u2010Tetrahydrocannabinoids**"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"http:\/\/orcid.org\/0000-0001-5347-4662","authenticated-orcid":false,"given":"Caroline","family":"Dorsch","sequence":"first","affiliation":[{"name":"Department of Chemistry and Mineralogy Universit\u00e4t Leipzig  Johannisallee 29 04103 Leipzig Germany"}]},{"ORCID":"http:\/\/orcid.org\/0000-0001-7392-9556","authenticated-orcid":false,"given":"Christoph","family":"Schneider","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Mineralogy Universit\u00e4t Leipzig  Johannisallee 29 04103 Leipzig Germany"}]}],"member":"311","published-online":{"date-parts":[[2023,5,5]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2006.05.034"},{"key":"e_1_2_3_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB00464B"},{"key":"e_1_2_3_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)86745-X"},{"key":"e_1_2_3_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408380"},{"key":"e_1_2_3_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.1c00513"},{"key":"e_1_2_3_6_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.50.1390"},{"key":"e_1_2_3_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol702692q"},{"key":"e_1_2_3_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/np020176"},{"key":"e_1_2_3_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol902840x"},{"key":"e_1_2_3_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6NP00074F"},{"key":"e_1_2_3_11_1","unstructured":"\u00a0"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.5012\/bkcs.2010.31.9.2712"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.07.033"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.05.005"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39890001171"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH9842339"},{"key":"e_1_2_3_17_1","unstructured":"Review:"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1055\/a-1781-6538"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c00588"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201913603"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c01375"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b00860"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201809692"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01865"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03311"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201509247"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201406044"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403573"},{"key":"e_1_2_3_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar500330x"},{"key":"e_1_2_3_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201607828"},{"key":"e_1_2_3_31_1","unstructured":"\u00a0"},{"key":"e_1_2_3_32_2","first-page":"3","volume-title":"Asymmetric Organocatalysis. New Strategies, Catalysts, and Opportunities, Vol.\u20051","author":"Dorsch C.","year":"2023"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201900932"},{"key":"e_1_2_3_34_1","unstructured":"\u00a0"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c04261"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202115036"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c00249"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c07447"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-021-00714-x"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c06677"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b07092"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09129"},{"key":"e_1_2_3_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/np0102861"},{"key":"e_1_2_3_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00433a020"},{"key":"e_1_2_3_45_1","unstructured":"1-Aryl terpenols1had to be purified on deactivated silica gel to prevent the formation of cinnamyl alcohol1\u2032.1\u2009iwas isolated as a mixture of both species (1\u2009i\/1\u2009i\u2032=1.5\u2009:\u20091 see the Supporting Information)."},{"key":"e_1_2_3_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00210a025"},{"key":"e_1_2_3_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c02665"},{"key":"e_1_2_3_48_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-023-05747-9"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202302475","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,1,12]],"date-time":"2024-01-12T05:03:42Z","timestamp":1705035822000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202302475"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,5,5]]},"references-count":48,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2023,6,12]]}},"alternative-id":["10.1002\/anie.202302475"],"URL":"http:\/\/dx.doi.org\/10.1002\/anie.202302475","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":["General Chemistry","Catalysis"],"published":{"date-parts":[[2023,5,5]]},"assertion":[{"value":"2023-02-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-05-05","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}