Catalytic Enantioselective Total Synthesis of (+)-Lycoperdic Acid
| Autor: | Sami Kortet, Petri M. Pihko, Aurélie Claraz |
|---|---|
| Přispěvatelé: | University of Jyväskylä (JYU) |
| Rok vydání: | 2020 |
| Předmět: |
Stereochemistry
aminohapot 010402 general chemistry 01 natural sciences Biochemistry Catalysis Hydrolysis chemistry.chemical_compound Lactones Lycoperdic acid Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS kemiallinen synteesi Molecular Structure 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Enantioselective synthesis Total synthesis Stereoisomerism 0104 chemical sciences katalyysi Azide Imines |
| Zdroj: | Organic Letters Organic Letters, American Chemical Society, 2020, 22 (8), pp.3010-3013. ⟨10.1021/acs.orglett.0c00772⟩ |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A concise enantio- and stereocontrolled synthesis of (+)-lycoperdic acid is presented. The stereochemical control is based on iminium-catalyzed Mukaiyama–Michael reaction and enamine-catalyzed organocatalytic α-chlorination steps. The amino group was introduced by azide displacement, affording the final stereochemistry of (+)-lycoperdic acid. Penultimate hydrogenation and hydrolysis afforded pure (+)-lycoperdic acid in seven steps from a known silyloxyfuran. peerReviewed |
| Databáze: | OpenAIRE |
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