ArticleNature chemistry2021
Mimicking oxidative radical cyclizations of lignan biosynthesis using redox-neutral photocatalysis.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Divergent synthesis of Haplomitrium diterpenoids via a late-stage biomimetic skeletal reorganization approach.Nature communications · 2025Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Insights into angiosperm evolution and lineage-specialized lignan biosynthesis from the early-divergingScience advances · 2025Article
- Stereoselective Synthesis of Benzoylated Gulmirecin A and Disciformycin B.Organic letters · 2025Article
- Cyclization by Intramolecular Suzuki-Miyaura Cross-Coupling-A Review.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024Article
- Combining the best of both worlds: radical-based divergent total synthesis.Beilstein journal of organic chemistry · 2023Review
- Phytophenol Dimerization Reaction: From Basic Rules to Diastereoselectivity and Beyond.Molecules (Basel, Switzerland) · 2022Article
- Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products.Chemical science · 2021Article
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2 authors.
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No grant is acknowledged in the PubMed record.
Abstract
Oxidative cyclizations create many unique chemical structures that are characteristic of biologically active natural products. Many of these reactions are catalysed by 'non-canonical' or 'thwarted' iron oxygenases and appear to involve long-lived radicals. Mimicking these biosynthetic transformations with chemical equivalents has been a long-standing goal of synthetic chemists but the fleeting nature of radicals, particularly under oxidizing conditions, makes this challenging. Here we use redox-neutral photocatalysis to generate radicals that are likely to be involved in the biosynthesis of lignan natural products. We present the total syntheses of highly oxidized dibenzocyclooctadienes, which feature densely fused, polycyclic frameworks that originate from a common radical progenitor. We show that multiple factors control the fate of the proposed biosynthetic radicals, as they select between 5- or 11-membered ring cyclizations and a number of different terminating events. Our syntheses create new opportunities to explore the medicinal properties of these natural products, while shedding light on their biosynthetic origin.
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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.