ArticleJournal of the American Chemical Society2021
Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "Strictosidyne" and "Strictosamidyne".
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- The Diels-Alder Reaction as a Key Step in Natural Product Synthesis.Progress in the chemistry of organic natural products · 2026Review
- Mechanisms of Kobayashi eliminations for the generation of highly strained arynes, cyclic cumulenes, and anti-Bredt olefins.Chemical science · 2025Article
- In vitro synthetic polyploidization and enhancement of anticancer compounds in Catharanthus Roseus (L.) G. Don important cultivars.Scientific reports · 2025Article
- Recent advancements in the chemistry of Diels-Alder reaction for total synthesis of natural products: a comprehensive review (2020-2023).RSC advances · 2025Review
- Investigations via Kinetics and Multivariate Linear Regression Models of the Mechanism and Origins of Regioselectivity in a Palladium-Catalyzed Aryne Annulation.ACS catalysis · 2024Article
- Collective total synthesis of stereoisomeric yohimbine alkaloids.Nature communications · 2024Article
- Aryne-Enabled C-N Arylation of Anilines.Angewandte Chemie (International ed. in English) · 2023Article
- Ligand-Induced Regioselectivity in Metal-Catalyzed Aryne Reactions Using Borylaryl Triflates as Aryne Precursors.Organometallics · 2023Article
- Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels-Alder Cycloaddition.Angewandte Chemie (International ed. in English) · 2022Article
- Chimeric natural products derived from medermycin and the nature-inspired construction of their polycyclic skeletons.Nature communications · 2022Article
- Engineered Production of Strictosidine and Analogues in Yeast.ACS synthetic biology · 2022Article
- Review
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Authors and funding
9 authors.
Funding
Abstract
Monoterpene indole alkaloids are a large class of natural products derived from a single biosynthetic precursor, strictosidine. We describe a synthetic approach to strictosidine that relies on a key facially selective Diels-Alder reaction between a glucosyl-modified alkene and an enal to set the C15-C20-C21 stereotriad. DFT calculations were used to examine the origin of stereoselectivity in this key step, wherein two of 16 possible isomers are predominantly formed. These calculations suggest the presence of a glucosyl unit, also inherent in the strictosidine structure, guides diastereoselectivity, with the reactive conformation of the vinyl glycoside dienophile being controlled by an
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