Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid
Kortet, Sami; Claraz, Aurélie; Pihko, Petri M. (2020). Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid. Organic Letters, 22 (8), 3010-3013. DOI: 10.1021/acs.orglett.0c00772
Published inOrganic Letters
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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.