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Evolution of a Strategy for Concise Enantioselective Total Synthesis of the Salinosporamide Family of Natural Products
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Park, Soojun | - |
dc.contributor.author | Lee, Jiwoo | - |
dc.contributor.author | Kim, Jae Hyun | - |
dc.contributor.author | Jeong, Yeji | - |
dc.contributor.author | Lee, Seokwoo | - |
dc.contributor.author | Lee, Su Won | - |
dc.contributor.author | Kim, Sanghee | - |
dc.date.accessioned | 2022-11-22T09:00:11Z | - |
dc.date.available | 2022-11-22T09:00:11Z | - |
dc.date.created | 2022-10-18 | - |
dc.date.issued | 2022-10 | - |
dc.identifier.citation | Angewandte Chemie - International Edition, Vol.61 No.41, p. e202210317 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | https://hdl.handle.net/10371/187177 | - |
dc.description.abstract | Our first strategy for rapidly accessing pyrrolidinone cores of salinosporamides involved combined use of memory of chirality and dynamic kinetic resolution principles in aldol reactions of the serine-derived 5-oxazolidinone substrate, which was ultimately unsuccessful with respect to enantioselectivity. This failure led us to the revised strategy. The influence of the stereocenter in 5-oxazolidinone enabled selective installation of the C-2 stereocenter. The intramolecular aldol reaction of the C-2 stereodefined aldol substrate was successful. An unexpected hydrolytic dynamic kinetic resolution was observed in hydrolyses of the bicyclic aldol products. This unprecedented substrate-driven hydrolytic dynamic kinetic resolution was utilized in preparing the pyrrolidinone core with excellent efficiency. Through this strategy, the concise total syntheses of salinosporamides A and B as well as cinnabaramides A, E, and F were achieved with high selectivity. | - |
dc.language | 영어 | - |
dc.publisher | John Wiley & Sons Ltd. | - |
dc.title | Evolution of a Strategy for Concise Enantioselective Total Synthesis of the Salinosporamide Family of Natural Products | - |
dc.type | Article | - |
dc.identifier.doi | 10.1002/anie.202210317 | - |
dc.citation.journaltitle | Angewandte Chemie - International Edition | - |
dc.identifier.wosid | 000849760000001 | - |
dc.identifier.scopusid | 2-s2.0-85137350915 | - |
dc.citation.number | 41 | - |
dc.citation.startpage | e202210317 | - |
dc.citation.volume | 61 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Kim, Sanghee | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
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