A Concise, Biomimetic Total Synthesis of (+)-Davanone

A Concise, Biomimetic Total Synthesis of (+)-Davanone

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...

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Veröffentlicht in:Organic letters 2009-05, Vol.11 (10), p.2217-2218
Hauptverfasser: Morrison, Karen C, Litz, Jonathan P, Scherpelz, Kathryn P, Dossa, Paul D, Vosburg, David A
Format: Artikel
Sprache:eng
Schlagworte:
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Artemisia - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Cyclization
Esterification
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
Parasympatholytics - chemical synthesis
Parasympatholytics - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
Thiazoles - chemistry
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Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900697w