ArticleOrganic letters2013
A redox economical synthesis of bioactive 6,12-guaianolides.
Article in Organic letters, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Bio-inspired total synthesis of daphnepapytone A.Chemical science · 2025Article
- Biological and Medicinal Properties ofInternational journal of molecular sciences · 2025Review
- Function-Oriented and Modular (+/-)-cis-Pseudoguaianolide Synthesis: Discovery of New Nrf2 Activators and NF-κB Inhibitors.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Synthesis of Guaianolide Analogues with a Tunable α-Methylene-γ-lactam Electrophile and Correlating Bioactivity with Thiol Reactivity.Journal of medicinal chemistry · 2020Article
- Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae.Journal of the American Chemical Society · 2019Article
- Stereoselective total synthesis of parthenolides indicates target selectivity for tubulin carboxypeptidase activity.Chemical science · 2019Article
- Molecular Basis for the N-Terminal Bromodomain-and-Extra-Terminal-Family Selectivity of a Dual Kinase-Bromodomain Inhibitor.Journal of medicinal chemistry · 2018Article
- A Double Allylation Strategy for Gram-Scale Guaianolide Production: Total Synthesis of (+)-Mikanokryptin.Angewandte Chemie (International ed. in English) · 2017Article
- Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction.Organic letters · 2016Article
- Synthesis and antileukemic activities of C1-C10-modified parthenolide analogues.Bioorganic & medicinal chemistry · 2015Article
- Conditions for a Rh(I)-catalyzed [2 + 2 + 1] cycloaddition reaction with methyl substituted allenes and alkynes.Tetrahedron letters · 2015Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Syntheses of two 6,12-guaianolide analogs are reported within. The scope of the tandem allylboration/lactonization chemistry is expanded to provide a functionalized allene-yne-containing α-methylene butyrolactone that undergoes a Rh(I)-catalyzed cyclocarbonylation reaction to afford a 5-7-5 ring system. The resulting cycloadducts bear a structural resemblance to other NF-κB inhibitors such as cumambrin A and indeed were shown to inhibit NF-κB signaling and cancer cell growth.
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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.