ArticleOrganic & biomolecular chemistry2021
Synthesis of illudalic acid and analogous phosphatase inhibitors.
Article in Organic & biomolecular chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 12 citations in OpenAlex.
- Regioselective [2 + 2 + 2] Alkyne Cyclotrimerizations to Hexasubstituted Benzenes: Syntheses of Fomajorin D and Fomajorin S.The Journal of organic chemistry · 2024Article
- The mechanism of covalent inhibition of LAR phosphatase by illudalic acid.Bioorganic & medicinal chemistry letters · 2024Article
- Selective hydrolysis of α-oxo keteneBeilstein journal of organic chemistry · 2024Article
- Derivatives of the Fungal Natural Product Illudalic Acid Inhibit the Activity of Protein Histidine Phosphatase PHPT1.ChemMedChem · 2023Article
- Small Molecules Targeting PTPσ-Trk Interactions Promote Sympathetic Nerve Regeneration.ACS chemical neuroscience · 2022Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Developing an efficient, concise synthesis of the fungal natural product illudalic acid has been a long-standing challenge, made more pressing by the recent discovery that illudalic acid and analogs are selective phosphatase inhibitors. Syntheses of illudalic acid have become progressively more efficient over the decades yet remain strategically grounded in a 17-step synthesis reported in 1977. Here we validate a two-step process-convergent [4 + 2] benzannulation and one-pot coordinated functional group manipulations-for preparing the key trifunctional pharmacophore of illudalic acid. The modular building blocks are readily available in 2-3 steps, for a longest linear sequence (LLS) of 5 steps to illudalic acid from 3,3-dimethylcyclopentanone. A small collection of analogous indanes and tetralins featuring the same pharmacophore were prepared by a similar route. These compounds potently and selectively inhibit the human leukocyte common antigen-related (LAR) subfamily of protein tyrosine phosphatases (PTPs). Evidence supporting a postulated covalent ligation mechanism is provided herein.
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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.