ArticleNature chemistry2020
Total synthesis of brevianamide A.
Article in Nature chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 89 citations in OpenAlex.
- Chemically guided single-cell transcriptomics reveals sulfotransferase-mediated scaffold remodeling in securinine biosynthesis.Nature communications · 2026Article
- The Diels-Alder Reaction as a Key Step in Natural Product Synthesis.Progress in the chemistry of organic natural products · 2026Review
- Divergent synthesis of Haplomitrium diterpenoids via a late-stage biomimetic skeletal reorganization approach.Nature communications · 2025Article
- Decoding theJournal of agricultural and food chemistry · 2025Article
- Engineering a Biosynthetic Pathway to Produce (+)-Brevianamides A and B.ACS catalysis · 2025Article
- Total Synthesis of Brevianamide S.Organic letters · 2025Article
- Total Synthesis of (-)-Elodeoidins A and B.JACS Au · 2025Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Recent advancements in the chemistry of Diels-Alder reaction for total synthesis of natural products: a comprehensive review (2020-2023).RSC advances · 2025Review
- Total Synthesis of (±)-Baphicacanthcusine A Enabled by Sequential Ring Contractions.Angewandte Chemie (International ed. in English) · 2024Article
- Catalytic Asymmetric Cyclizative Rearrangement of Anilines and Vicinal Diketones to Access 2,2-Disubstituted Indolin-3-ones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels-Alder Cycloaddition.Angewandte Chemie (International ed. in English) · 2022Article
- One-pot synthesis of 2,5-diketopiperazine with high titer and versatility using adenylation enzyme.Applied microbiology and biotechnology · 2022Article
- New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds.Chembiochem : a European journal of chemical biology · 2022Review
- Unified total synthesis of the brevianamide alkaloids enabled by chemical investigations into their biosynthesis.Chemical science · 2022Article
- Synthesis of (±)-Setigerumine I: Biosynthetic Origins of the Elusive Racemic Papaveraceae Isoxazolidine Alkaloids*.Angewandte Chemie (International ed. in English) · 2021Article
- A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C.Chemical science · 2021Article
- Accelerating Reaction Rates of Biomolecules by Using Shear Stress in Artificial Capillary Systems.Journal of the American Chemical Society · 2021Article
- Recent development and applications of semipinacol rearrangement reactions.Chemical science · 2021Review
- Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.ACS central science · 2021Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The fungal-derived bicyclo[2.2.2]diazaoctane alkaloids are of interest to the scientific community for their potent and varied biological activities. Within this large and diverse family of natural products, the insecticidal metabolite (+)-brevianamide A is particularly noteworthy for its synthetic intractability and inexplicable biogenesis. Despite five decades of research, this alkaloid has remained an elusive target for chemical synthesis due to insurmountable issues of reactivity and selectivity associated with all previously explored strategies. We herein report the chemical synthesis of (+)-brevianamide A (seven steps, 7.2% overall yield, 750 mg scale), which involves a bioinspired cascade transformation of the linearly fused (-)-dehydrobrevianamide E into the topologically complex bridged-spiro-fused structure of (+)-brevianamide A.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.