Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 40, Pages 17556-17564Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005151
Keywords
alkaloids; alkylation; cooperative catalysis; iridium; palladium
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Funding
- National Institutes of Health [R01GM121573]
- IU Vice Provost for Research through the Research Equipment Fund
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We describe enantioselective syntheses ofstrychnosandchelidoniumalkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed alpha-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (-)-akuammicine and (-)-strychnine. In the second case, the poor performance ofortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed alpha-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.
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