Brønsted acid promoted intramolecular cyclization of O-alkynyl benzoic acids: Concise total synthesis of exserolide F
| Autor: | Mohan Dumpala, Palakodety Radha Krishna, Lingaswamy Kadari |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Isocoumarins Regioselectivity Total synthesis 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Stereoselectivity Brønsted–Lowry acid–base theory Triflic acid Benzoic acid |
| DOI: | 10.6084/m9.figshare.6981800 |
| Popis: | Herein we report the stereoselective total synthesis of Exserolide F. The key step involves triflic acid catalyzed highly regioselective intramolecular cyclization of an O-alkynyl benzoic acid derivative to accomplish the core isocoumarin skeleton of the natural product via 6-endo-dig mode of cyclization. The other important steps are: Sharpless asymmetric epoxidation, Barbier propargylation, Sonogashira coupling en route to access the O-alkynyl benzoic acid derivative. |
| Databáze: | OpenAIRE |
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