ArticleOrganic & biomolecular chemistry2014
ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions: synthesis of dihydropyran-fused diterpenoids.
Article in Organic & biomolecular chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Recent advances in oridonin derivatives with anticancer activity.Frontiers in chemistry · 2023Review
- Unified, Asymmetric Total Synthesis of the Asnovolins and Related Spiromeroterpenoids: A Fragment Coupling Approach.Journal of the American Chemical Society · 2022Article
- Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffoldsRSC advances · 2022Article
- Oridonin and its derivatives for cancer treatment and overcoming therapeutic resistance.Genes & diseases · 2021Review
- Enantioselective Type II Cycloaddition of Alkynes via C-C Activation of Cyclobutanones: Rapid and Asymmetric Construction of [3.3.1] Bridged Bicycles.Journal of the American Chemical Society · 2020Article
- Design and synthesis of novel oridonin analogues as potent anticancer agents.Journal of enzyme inhibition and medicinal chemistry · 2018Article
- Structural modification of oridoninRSC advances · 2018Article
- Regio- and Stereospecific Synthesis of Oridonin D-Ring Aziridinated Analogues for the Treatment of Triple-Negative Breast Cancer via Mediated Irreversible Covalent Warheads.Journal of medicinal chemistry · 2018Article
- Therapeutic Potential of Oridonin and Its Analogs: From Anticancer and Antiinflammation to Neuroprotection.Molecules (Basel, Switzerland) · 2018Review
- Discovery and development of natural product oridonin-inspired anticancer agents.European journal of medicinal chemistry · 2016Review
- Targeting XBP1-mediated β-catenin expression associated with bladder cancer with newly synthetic Oridonin analogues.Oncotarget · 2016Article
- Oridonin, a Promising ent-Kaurane Diterpenoid Lead Compound.International journal of molecular sciences · 2016Review
- Enhanced effects of novel oridonin analog CYD0682 for hepatic fibrosis.The Journal of surgical research · 2015Article
- Enhanced anti-fibrogenic effects of novel oridonin derivative CYD0692 in hepatic stellate cells.Molecular and cellular biochemistry · 2015Article
- Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents.European journal of medicinal chemistry · 2015Review
- Effect of natural and semisynthetic pseudoguianolides on the stability of NF-κB:DNA complex studied by agarose gel electrophoresis.PloS one · 2015Article
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Authors and funding
10 authors.
Funding
Abstract
A mild and concise approach for the construction of a 3,4-dihydro-2H-pyran ring integrated into the A-ring of the natural product oridonin using an optimized inverse electron demand hetero-Diels-Alder (IED HDA) reaction is reported herein. A self-dimerization of the exocyclic enone installed in the A-ring through a homo-HDA reaction was identified to exclusively give a dimeric ent-kaurane diterpenoid with the spirochroman core. Moreover, efficient cross-HDA cycloadditions of this enone with various vinyl ethers or vinyl sulfides, instead of its own homo-HDA dimerization, were achieved in a regio- and stereoselective manner, thus providing access to novel dihydropyran-fused diterpenoids as potential anticancer agents to overcome chemoresistance.
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