Short Total Synthesis of (±)-[gamma]-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

Short Total Synthesis of (±)-[gamma]-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-[gamma]-lycorane, incorporating a new intram...

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Veröffentlicht in:Chemistry : a European journal 2017-04, Vol.23 (20), p.4750
Hauptverfasser: Monaco, Alessandra, Szulc, Blanka R, Rao, Zenobia X, Barniol-Xicota, Marta, Sehailia, Moussa, Borges, Bruno M A, Hilton, Stephen T
Format: Artikel
Sprache:eng
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Chemistry
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Zusammenfassung:An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-[gamma]-lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201700143