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Evolution of a Strategy for Concise Enantioselective Total Synthesis of the Salinosporamide Family of Natural Products
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Cited 4 time in Scopus
- Authors
- Issue Date
- 2022-10
- Publisher
- John Wiley & Sons Ltd.
- Citation
- Angewandte Chemie - International Edition, Vol.61 No.41, p. e202210317
- 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.
- ISSN
- 1433-7851
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