ArticleOrganic letters2009
Enantioselective total synthesis of (-)-pironetin: iterative aldol reactions of thiazolidinethiones.
Article in Organic letters, 2009. 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, 67 citations in OpenAlex.
- Dual Ruthenium-Catalyzed Alkene Isomerization-Hydrogen Auto-Transfer Unlocks Skipped Dienes as Pronucleophiles for Enantioselective Alcohol C-H Allylation.Journal of the American Chemical Society · 2023Article
- Molecular Docking of Cryptoconcatones to α-Tubulin and Related Pironetin Analogues.Plants (Basel, Switzerland) · 2023Article
- Cytotoxicity of phenylpironetin analogs and the metabolic fate of pironetin and phenylpironetin.Bioorganic chemistry · 2022Article
- Diastereoselective Substitution Reactions of Acyclic β-Alkoxy Acetals via Electrostatically Stabilized Oxocarbenium Ion Intermediates.Organic letters · 2022Article
- The Synthesis of 3-(Molecules (Basel, Switzerland) · 2022Article
- Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics.Bioorganic & medicinal chemistry letters · 2019Review
- Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin.ChemMedChem · 2017Article
- Bioinspired iterative synthesis of polyketides.Frontiers in chemistry · 2015Review
- The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.Organic letters · 2014Article
- Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.Organic letters · 2012Article
- 1-[(4S)-4-Benzyl-2-thioxo-1,3-thia-zol-idin-3-yl]propan-1-one.Acta crystallographica. Section E, Structure reports online · 2009Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The enantioselective total synthesis of pironetin has been achieved in 11 steps from known aldehyde 2. The synthesis relies on the formation of 5 out of 6 stereocenters through titanium mediated iterative aldol reactions. Key steps in this synthesis include an acetal aldol reaction to establish the stereochemistry at C8 and C9, an acetate aldol reaction, and "Evans" syn aldol reaction.
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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.