{"title":"利用对映体选择性金催化生产 C3a-芳基取代的氢吲哚生物碱的综合方法","authors":"Jhen Kuei Yu, Constantin Czekelius","doi":"10.1055/s-0043-1775389","DOIUrl":null,"url":null,"abstract":"<p>A diversity-oriented total synthesis for <i>Amaryllidaceae</i> alkaloids incorporating the frequently found C3a-arylated hydroindole moiety was developed. Chiral-anion-induced gold(I) catalysis was employed for the cyclization of 1,4-diynes to the pyrrolidine and the installation of the all-carbon quaternary stereocenter. Both enantiomeric series of crinine-type alkaloids in high enantiopurity were accessible by this methodology. The formal synthesis of a wide range of <i>Amaryllidaceae</i> alkaloids is described, such as (+)-vitattine, (–)-<i>epi</i>-vitattine, (–)-elwesein, (–)-<i>epi</i>-elwesein, (–)-crinine, (–)-<i>epi</i>-crinine, (–)-buphanisine, (–)-flexinine, and (+)-gracilamine.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"3 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A Comprehensive Approach to C3a-Aryl-Substituted Hydroindole Alkaloids by Utilizing Enantioselective Gold Catalysis\",\"authors\":\"Jhen Kuei Yu, Constantin Czekelius\",\"doi\":\"10.1055/s-0043-1775389\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>A diversity-oriented total synthesis for <i>Amaryllidaceae</i> alkaloids incorporating the frequently found C3a-arylated hydroindole moiety was developed. Chiral-anion-induced gold(I) catalysis was employed for the cyclization of 1,4-diynes to the pyrrolidine and the installation of the all-carbon quaternary stereocenter. Both enantiomeric series of crinine-type alkaloids in high enantiopurity were accessible by this methodology. The formal synthesis of a wide range of <i>Amaryllidaceae</i> alkaloids is described, such as (+)-vitattine, (–)-<i>epi</i>-vitattine, (–)-elwesein, (–)-<i>epi</i>-elwesein, (–)-crinine, (–)-<i>epi</i>-crinine, (–)-buphanisine, (–)-flexinine, and (+)-gracilamine.</p> \",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":\"3 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-08-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/s-0043-1775389\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/s-0043-1775389","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
A Comprehensive Approach to C3a-Aryl-Substituted Hydroindole Alkaloids by Utilizing Enantioselective Gold Catalysis
A diversity-oriented total synthesis for Amaryllidaceae alkaloids incorporating the frequently found C3a-arylated hydroindole moiety was developed. Chiral-anion-induced gold(I) catalysis was employed for the cyclization of 1,4-diynes to the pyrrolidine and the installation of the all-carbon quaternary stereocenter. Both enantiomeric series of crinine-type alkaloids in high enantiopurity were accessible by this methodology. The formal synthesis of a wide range of Amaryllidaceae alkaloids is described, such as (+)-vitattine, (–)-epi-vitattine, (–)-elwesein, (–)-epi-elwesein, (–)-crinine, (–)-epi-crinine, (–)-buphanisine, (–)-flexinine, and (+)-gracilamine.
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