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Total Synthesis of (+)-Alsmaphorazine C
Total Synthesis of (+)-Alsmaphorazine C and Formal Synthesis of (+)-Strictamine: A Photo-Fries Approach.
Angew. Chem. Int. Ed. 2021;
Key words(+)-alsmaphorazine C - photo-Fries reaction - indole alkaloids - van Leusen reaction - continuous-flow chemistry
In 2012, Morita and co-workers isolated the indole alkaloid (+)-alsmaphorazine C from the leaves of Alstonia pneumatophore. Ding and co-workers present the first and asymmetric synthesis of this intriguing natural product.
Hydroxy ketone F was quickly accessed from tryptamine A in four steps. The key photo-Fries reaction/addition to imine cascade gave complex tetracycle G in 55% yield. Further elaboration of this intermediate gave the natural product in a total of 14 steps.
18 May 2021 (online)
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