{"title":"Synthesis of (−)-Monanchoradin A and (−)-Crambescin A2 392 Based on a Cyclization–Carbonylation–Cyclization Cascade","authors":"Takuya Tsukamoto, Keisuke Takahashi, Natsuki Murase, Kyoka Someya, Fujino Sakata, Tianci Yue, Taichi Kusakabe, Keisuke Kato","doi":"10.1021/acs.orglett.4c03158","DOIUrl":null,"url":null,"abstract":"Syntheses of guanidino alkaloids (−)-monanchoradin A and (−)-crambescin A2 392 are described. The key feature of the syntheses is the cyclization–carbonylation–cyclization cascade of the optically active propargyl guanidine. The bicyclic guanidino cores bearing an asymmetric center and ester or carboxylic acid functionality were constructed in a single step. The carboxylic acid was then converted to (−)-monanchoradin A and (−)-crambescin A2 392.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c03158","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Syntheses of guanidino alkaloids (−)-monanchoradin A and (−)-crambescin A2 392 are described. The key feature of the syntheses is the cyclization–carbonylation–cyclization cascade of the optically active propargyl guanidine. The bicyclic guanidino cores bearing an asymmetric center and ester or carboxylic acid functionality were constructed in a single step. The carboxylic acid was then converted to (−)-monanchoradin A and (−)-crambescin A2 392.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.