ArticleJournal of natural medicines2021
One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme.
Article in Journal of natural medicines, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Bifunctional Monothiosquaramide-Catalyzed Enantioselective Addition of Masked Acyl Cyanide to Isatins: Umpolung Strategy for the Total Synthesis of (Organic letters · 2026Article
- Mechanistic Perspective on C-N and C-S Bond Construction Catalyzed by Cytochrome P450 Enzymes.ACS bio & med chem Au · 2025Review
- Isolation and Identification of Herbicidal Active Compounds fromPlants (Basel, Switzerland) · 2023Article
- 2-Oxindole and related heterocycles: synthetic methodologies for their natural products and related derivatives.RSC advances · 2023Review
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Authors and funding
4 authors.
Funding
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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Registered trials
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