ArticleJournal of the American Chemical Society2014
Total synthesis of tetrahydrolipstatin and stereoisomers via a highly regio- and diastereoselective carbonylation of epoxyhomoallylic alcohols.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Orlistat: a comprehensive review of a lipase inhibitor from obesity management to emerging oncological applications.Frontiers in pharmacology · 2026Review
- Advances in Catalyst Design for β-Lactone Formation via Ring-Expansion Carbonylation.Molecules (Basel, Switzerland) · 2025Review
- Draft genome sequence of3 Biotech · 2023Article
- RhJournal of the American Chemical Society · 2021Article
- Total Synthesis of Tetrahydrolipstatin, Its Derivatives, and Evaluation of Their Ability to Potentiate Multiple Antibiotic Classes againstACS infectious diseases · 2021Article
- Total and Formal Syntheses of Fostriecin.Organic chemistry frontiers : an international journal of organic chemistry · 2020Article
- New strategies and structural considerations in development of therapeutics for carbapenem-resistant Enterobacteriaceae.Translational research : the journal of laboratory and clinical medicine · 2020Review
- Synthesis and direct comparison of the anticancer activities of phomopsolides D and E and two 7-oxa-/7-aza-analogues.MedChemComm · 2019Article
- Development and Optimization of a High-Throughput Screening Assay for Rapid Evaluation of Lipstatin Production by Streptomyces Strains.Current microbiology · 2018Article
- Characterization of Tetrahydrolipstatin and Stereoderivatives on the Inhibition of Essential Mycobacterium tuberculosis Lipid Esterases.Biochemistry · 2018Article
- Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin.ACS medicinal chemistry letters · 2018Article
- Natural Dietary and Herbal Products in Anti-Obesity Treatment.Molecules (Basel, Switzerland) · 2016Review
- Combining cross-metathesis and activity-based protein profiling: new β-lactone motifs for targeting serine hydrolases.Bioorganic & medicinal chemistry letters · 2015Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
A concise enantioselective synthesis of tetrahydrolipstatin (THL) and seven stereoisomers has been achieved. The synthesis of THL was accomplished in 10 steps and 31% overall yield from an achiral ynone. Key to the success of the approach is the use of a bimetallic [Lewis acid](+)[Co(CO)4](-) catalyst for a late-stage regioselective carbonylation of an enantiomerically pure cis-epoxide to a trans-β-lactone. The success of this route to THL and its stereoisomers also demonstrated the practicality of the carbonylation catalyst for complex molecule synthesis as well as its functional group compatibility.
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