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Enantioselective modular synthesis of cyclohexenones: total syntheses of (+)-crypto- and (+)-cnfectocaryone

A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the w...

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Hauptverfasser: Franck, Géraldine Julie Anne-Marie (VerfasserIn) , Brödner, Kerstin (VerfasserIn) , Helmchen, Günter (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: August 02, 2010
In: Organic letters
Year: 2010, Jahrgang: 12, Heft: 17, Pages: 3886-3889
ISSN:1523-7052
DOI:10.1021/ol101588j
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/ol101588j
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Verfasserangaben:Géraldine Franck, Kerstin Brödner, Günter Helmchen
Beschreibung
Zusammenfassung:A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the way to (+)-cryptocaryone, a catch and release strategy involving an iodolactonization/elimination and a regioselective C-acylation were used.
Beschreibung:Gesehen am 07.11.2023
Beschreibung:Online Resource
ISSN:1523-7052
DOI:10.1021/ol101588j

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