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Asymmetric Total Syntheses of the Akuammiline Alkaloids (-)-Strictamine and (-)-Rhazinoline.
Angewandte Chemie 2019 Februrary 19
Strictamine and rhazinoline are representative methanoquinolizidine-containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a photocatalytic intra/intermolecular type II radical cascade reaction, a Tsuji-Trost allylation, a palladium- or nickel-mediated cyclization, and a late-stage intramolecular N-alkylation reaction.
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