Versatile Approaches for the Synthesis of Fused-Ring γ‑Lactones Utilizing Cyclopropane Intermediates

Versatile Approaches for the Synthesis of Fused-Ring γ‑Lactones Utilizing Cyclopropane Intermediates

A highly effective acid-catalyzed cyclopropyl ester to γ-lactone skeletal rearrangement has been demonstrated and applied to the synthesis of a variety of bi- and tricyclic functionalized lactones, rigid and highly compact structures for use as biological probes.

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Veröffentlicht in:Organic letters 2013-04, Vol.15 (7), p.1591-1593
Hauptverfasser: Newhouse, Timothy R, Kaib, Philip S. J, Gross, Andrew W, Corey, E. J
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Crystallography, X-Ray
Cyclopropanes - chemistry
Esters
Lactones - chemical synthesis
Lactones - chemistry
Molecular Conformation
Molecular Structure
Stereoisomerism
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Beschreibung
Zusammenfassung:A highly effective acid-catalyzed cyclopropyl ester to γ-lactone skeletal rearrangement has been demonstrated and applied to the synthesis of a variety of bi- and tricyclic functionalized lactones, rigid and highly compact structures for use as biological probes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400362t