ArticleJournal of the American Chemical Society2023
Total Synthesis of Strempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono-Mannich Reaction.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Copper-Catalyzed Petasis-Type Reaction Enables Efficient Synthesis of C1-Substituted Tetrahydro-β-carbolines.Organic letters · 2026Article
- Pyrazolylpyrimidinamines Decorated via Petasis Reaction as Small-Molecule Activators of the RNA-Degrading Ribonuclease IRE1α.ACS bio & med chem Au · 2026Article
- Intercepting an avoided α-iminol rearrangement with a Petasis reaction for the synthesis of 2,3-diaryl substituted indoles.Communications chemistry · 2025Article
- Pd-catalyzed enantioselective access to hydrocarbazolones containing contiguous quaternary and tertiary stereocenters.Chemical science · 2025Article
- The Petasis Reaction: Applications and Organic Synthesis-A Comprehensive Review.Topics in current chemistry (Cham) · 2025Review
- Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Enantioselective Total Synthesis of (-)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy.Journal of the American Chemical Society · 2024Article
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Authors and funding
5 authors.
Funding
Abstract
Strempeliopidine is a member of the monoterpenoid bisindole alkaloid family, a class of natural products that have been shown to elicit an array of biological responses including modulating protein-protein interactions in human cancer cells. Our synthesis of strempeliopidine leverages palladium-catalyzed decarboxylative asymmetric allylic alkylations to install the requisite all-carbon quaternary centers found in each of the two monomeric natural products, aspidospermidine and eburnamine. Initial studies employing Suzuki-Miyaura cross-coupling followed by diastereoselective hydrogenation provided evidence for a structural reassignment of the natural product. Our final synthetic sequence employs a diastereoselective Petasis borono-Mannich reaction to couple eburnamine to a trifluoroborate aspidospermidine derivative. These convergent approaches enabled the synthesis of eight diastereomers of this heterodimer and offer support for the reassignment of the absolute configuration of strempeliopidine.
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