ArticleChemistry (Weinheim an der Bergstrasse, Germany)2011
Highly stereoselective total synthesis of fully hydroxy-protected mycolactones A and B and their stereoisomerization upon deprotection.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- Toward Understanding the Mechanism of Client-Selective Small Molecule Inhibitors of the Sec61 Translocon.Journal of molecular recognition : JMR · 2025Review
- Review
- Article
- Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis.Tetrahedron · 2018Article
- The chemistry and biology of mycolactones.Beilstein journal of organic chemistry · 2017Review
- Short Convergent Synthesis of the Mycolactone Core Through Lithiation-Borylation Homologations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Catalytic enantioselective synthesis of chiral organic compounds of ultra-high purity of >99% ee.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2015Review
- Negishi coupling: an easy progress for C-C bond construction in total synthesis.Molecular diversity · 2014Review
- Structure-activity relationship studies on the macrolide exotoxin mycolactone of Mycobacterium ulcerans.PLoS neglected tropical diseases · 2013Article
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3 authors.
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Abstract
Unprecedentedly efficient and highly (≥98 %) stereoselective syntheses of mycolactones A and B side chains relied heavily on Pd-catalyzed alkenylation (Negishi version) and were completed in 11 longest linear steps from ethyl (S)-3-hydroxybutyrate in 12% and 11% overall yield, respectively, roughly corresponding to an average of 82% yield per step. The synthesis of mycolactone core was realized by using Pd-catalyzed alkenyl-allyl coupling and an epoxide-opening reaction with a trialkylalkenylaluminate as key steps. Fully hydroxy-protected mycolactones A and B of ≥98% isomeric purity were synthesized successfully for the first time. However, unexpected 4:3-5:4 inseparable mixtures of mycolactones A and B were obtained upon deprotection.
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