6533b873fe1ef96bd12d4c40
RESEARCH PRODUCT
Catalytic Enantioselective Total Synthesis of (+)-Lycoperdic Acid.
Sami KortetPetri M. PihkoAurélie Clarazsubject
Stereochemistryaminohapot010402 general chemistry01 natural sciencesBiochemistryCatalysisCatalysisHydrolysischemistry.chemical_compoundLactonesLycoperdic acidPhysical and Theoretical ChemistryComputingMilieux_MISCELLANEOUSkemiallinen synteesiMolecular Structure010405 organic chemistryChemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic ChemistryEnantioselective synthesisTotal synthesisStereoisomerism0104 chemical scienceskatalyysiAzideIminesdescription
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
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-04-17 | Organic letters |