Synfacts 2021; 17(06): 0597
DOI: 10.1055/s-0040-1719737
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (+)-Alsmaphorazine C

Rezensent(en):
Erick M. Carreira
,
Hendrik Bulthaupt
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.
 

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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Publikationsverlauf

Publikationsdatum:
18. Mai 2021 (online)

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