{"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":null,"pages":null},"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}
引用次数: 0
Abstract
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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