Abstract
The enantioselective synthesis of (S)-(−)-spirobrassinin, which features a unique sulfur-containing spirooxindole skeleton, was achieved by focusing on the phytoalexin generation in Brassicaceae plants. Specifically, (S)-(−)-spirobrassinin was obtained in a one-pot fashion from l-tryptophan through a reaction involving S-spirocyclization with various turnip enzymes and constituents, i.e., using the turnip as a reaction reagent, catalyst, and reaction vessel. Surprisingly, this strategy also enabled the one-pot enantioselective synthesis of the novel non-natural spirooxindole (S)-(−)-5-methylspirobrassinin from 5-methyl-dl-tryptophan.
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Acknowledgements
This work was supported by JSPS KAKENHI Grants 18J22755 (to K. R.), 20K07109 (to S. Nakamura), and 20H03397 (to S. Nakamura).
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Ryu, K., Nakamura, S., Nakashima, S. et al. One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme. J Nat Med 75, 308–318 (2021). https://doi.org/10.1007/s11418-020-01468-9
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DOI: https://doi.org/10.1007/s11418-020-01468-9