ArticleThe Journal of organic chemistry2014
Enantioselective total syntheses of FR901464 and spliceostatin A and evaluation of splicing activity of key derivatives.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 37 citations in OpenAlex.
- Epigenetic Regulation and Therapeutic Targeting of Alternative Splicing Dysregulation in Cancer.Pharmaceuticals (Basel, Switzerland) · 2025Review
- Therapeutic Targeting of Alternative Splicing: A New Frontier in Cancer Treatment.Frontiers in oncology · 2022Review
- Spliceostatins and Derivatives: Chemical Syntheses and Biological Properties of Potent Splicing Inhibitors.Journal of natural products · 2021Review
- Total Synthesis of Meayamycin andOrganic letters · 2020Article
- Copper-Catalyzed Stille Cross-Coupling Reaction and Application in the Synthesis of the Spliceostatin Core Structure.The Journal of organic chemistry · 2020Article
- Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment.ACS medicinal chemistry letters · 2020Article
- Syntheses of spliceostatins and thailanstatins: a review.Beilstein journal of organic chemistry · 2020Review
- Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity.Organic letters · 2018Article
- Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction.Organic & biomolecular chemistry · 2018Article
- Nature Inspired Molecular Design: Stereoselective Synthesis of Bicyclic and Polycyclic Ethers for Potent HIV-1 Protease Inhibitors.Asian journal of organic chemistry · 2018Article
- Enantioselective Synthesis of Thailanstatin A Methyl Ester and Evaluation of in Vitro Splicing Inhibition.The Journal of organic chemistry · 2018Article
- Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester.Organic letters · 2018Article
- Modulating splicing with small molecular inhibitors of the spliceosome.Wiley interdisciplinary reviews. RNA · 2017Review
- Design, synthesis and in vitro splicing inhibition of desmethyl and carba-derivatives of herboxidiene.Organic & biomolecular chemistry · 2016Article
- Defining Viral Defective Ribosomal Products: Standard and Alternative Translation Initiation Events Generate a Common Peptide from Influenza A Virus M2 and M1 mRNAs.Journal of immunology (Baltimore, Md. : 1950) · 2016Article
- Interchangeable SF3B1 inhibitors interfere with pre-mRNA splicing at multiple stages.RNA (New York, N.Y.) · 2016Article
- Microbial and Natural Metabolites That Inhibit Splicing: A Powerful Alternative for Cancer Treatment.BioMed research international · 2016Review
- Enantioselective synthesis of spliceostatin E and evaluation of biological activity.Organic letters · 2014Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
FR901464 (1) and spliceostatin A (2) are potent inhibitors of spliceosomes. These compounds have shown remarkable anticancer activity against multiple human cancer cell lines. Herein, we describe efficient, enantioselective syntheses of FR901464, spliceostatin A, six corresponding diastereomers and an evaluation of their splicing activity. Syntheses of spliceostatin A and FR901464 were carried out in the longest linear sequence of 9 and 10 steps, respectively. To construct the highly functionalized tetrahydropyran A-ring, we utilized CBS reduction, Achmatowicz rearrangement, Michael addition, and reductive amination as key steps. The remarkable diastereoselectivity of the Michael addition was specifically demonstrated with different substrates under various reaction conditions. The side chain B was prepared from an optically active alcohol, followed by acetylation and hydrogenation over Lindlar's catalyst. The other densely functionalized tetrahydropyran C-ring was derived from readily available (R)-isopropylidene glyceraldehyde through a route featuring 1,2-addition, cyclic ketalization, and regioselective epoxidation. These fragments were coupled together at a late stage through amidation and cross-metathesis in a convergent manner. Six key diastereomers were then synthesized to probe the importance of specific stereochemical features of FR901464 and spliceostatin A, with respect to their in vitro splicing activity.
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