A Concise, Biomimetic Total Synthesis of (+)-Davanone
| Autor: | Paul D. Dossa, Kathryn P. Scherpelz, Karen C. Morrison, Jonathan P. Litz, David A. Vosburg |
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| Rok vydání: | 2009 |
| Předmět: |
inorganic chemicals
Antifungal Agents Stereoisomerism Biochemistry Catalysis chemistry.chemical_compound Biomimetic synthesis Organic chemistry Molecule Physical and Theoretical Chemistry Isoprene Biological Products Natural product Esterification Molecular Structure Organic Chemistry Parasympatholytics Total synthesis Thiazoles Artemisia chemistry Cyclization Stereoselectivity Oxidation-Reduction Sesquiterpenes Palladium |
| Zdroj: | Organic Letters. 11:2217-2218 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol900697w |
| Popis: | A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis. |
| Databáze: | OpenAIRE |
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