General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (+/-)-Antirhine, (+/-)-18,19-Dihydroantirhine, and Their 20-Epimers
DC Field | Value | Language |
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dc.contributor.author | Bae, Cheolwoo | - |
dc.contributor.author | Park, Eunjoon | - |
dc.contributor.author | Cho, Cheon-Gyu | - |
dc.contributor.author | Cheon, Cheol-Hong | - |
dc.date.accessioned | 2021-08-31T06:21:31Z | - |
dc.date.available | 2021-08-31T06:21:31Z | - |
dc.date.created | 2021-06-18 | - |
dc.date.issued | 2020-03-20 | - |
dc.identifier.issn | 1523-7060 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/57243 | - |
dc.description.abstract | A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (+/-)-antirhine, (+/-)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | INDOLE ALKALOIDS | - |
dc.subject | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject | DL-18,19-DIHYDROANTIRHINE | - |
dc.subject | (-)-ANTIRHINE | - |
dc.subject | DERIVATIVES | - |
dc.subject | SYNTHON | - |
dc.title | General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (+/-)-Antirhine, (+/-)-18,19-Dihydroantirhine, and Their 20-Epimers | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Cheon, Cheol-Hong | - |
dc.identifier.doi | 10.1021/acs.orglett.0c00544 | - |
dc.identifier.scopusid | 2-s2.0-85081657861 | - |
dc.identifier.wosid | 000526331100048 | - |
dc.identifier.bibliographicCitation | ORGANIC LETTERS, v.22, no.6, pp.2354 - 2358 | - |
dc.relation.isPartOf | ORGANIC LETTERS | - |
dc.citation.title | ORGANIC LETTERS | - |
dc.citation.volume | 22 | - |
dc.citation.number | 6 | - |
dc.citation.startPage | 2354 | - |
dc.citation.endPage | 2358 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.subject.keywordPlus | INDOLE ALKALOIDS | - |
dc.subject.keywordPlus | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject.keywordPlus | DL-18,19-DIHYDROANTIRHINE | - |
dc.subject.keywordPlus | (-)-ANTIRHINE | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | SYNTHON | - |
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