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Synfacts 2021; 17(06): 0597
DOI: 10.1055/s-0040-1719737
DOI: 10.1055/s-0040-1719737
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (+)-Alsmaphorazine C
Gao B,
Yao F,
Zhang Z,
Ding H.
*
Zhejiang University, Hangzhou, P. R. of China
Total Synthesis of (+)-Alsmaphorazine C and Formal Synthesis of (+)-Strictamine: A Photo-Fries Approach.
Angew. Chem. Int. Ed. 2021;
60: 10603-10607
DOI: 10.1002/anie.202101752
Total Synthesis of (+)-Alsmaphorazine C and Formal Synthesis of (+)-Strictamine: A Photo-Fries Approach.
Angew. Chem. Int. Ed. 2021;
60: 10603-10607
DOI: 10.1002/anie.202101752
Key words
(+)-alsmaphorazine C - photo-Fries reaction - indole alkaloids - van Leusen reaction - continuous-flow chemistry
Significance
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.
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Comment
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.
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Publication History
Article published online:
18 May 2021
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