ArticleThe Journal of organic chemistry2013
Emulating the logic of monoterpenoid alkaloid biogenesis to access a skeletally diverse chemical library.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Generation of the Camptothecin Scaffold by a Flavin-Catalyzed Photooxidative Skeletal Reorganization.Angewandte Chemie (International ed. in English) · 2026Article
- Unifying principles for the design and evaluation of natural product-inspired compound collections.Chemical science · 2025Review
- Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions.Angewandte Chemie (International ed. in English) · 2024Article
- Chemical Reactions of Indole Alkaloids That Enable Rapid Access to New Scaffolds for Discovery.SynOpen (2017) · 2023Article
- Recent Advances in Divergent Synthetic Strategies for Indole-Based Natural Product Libraries.Molecules (Basel, Switzerland) · 2022Review
- Site selective C-H functionalization of Mitragyna alkaloids reveals a molecular switch for tuning opioid receptor signaling efficacy.Nature communications · 2021Article
- Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.Organic letters · 2014Article
- Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.Journal of the American Chemical Society · 2014Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
We have developed a synthetic strategy that mimics the diversity-generating power of monoterpenoid indole alkaloid biosynthesis. Our general approach goes beyond diversification of a single natural product-like substructure and enables production of a highly diverse collection of small molecules. The reaction sequence begins with rapid and highly modular assembly of the tetracyclic indoloquinolizidine core, which can be chemoselectively processed into several additional skeletally diverse structural frameworks. The general utility of this approach was demonstrated by parallel synthesis of two representative chemical libraries containing 847 compounds with favorable physicochemical properties to enable its subsequent broad pharmacological evaluation.
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