Short Total Synthesis of (±)‐γ‐Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

• Published in: Chemistry : a European journal Vol. 23; no. 20; pp. 4750 - 4755
• Main Authors: Monaco, Alessandra, Szulc, Blanka R., Rao, Zenobia X., Barniol‐Xicota, Marta, Sehailia, Moussa, Borges, Bruno M. A., Hilton, Stephen T.
• Format: Journal Article
• Language: English
• Published: Germany 06.04.2017
• Subjects: Amaryllidaceae Alkaloids - chemical synthesis; Amaryllidaceae Alkaloids - chemistry; Catalysis; Coordination Complexes - chemistry; Coupling; Cyclization; erythrina; Heck reaction; Lewis acid; Lewis acids; Lewis Acids - chemistry; lycoranes; Methodology; Natural products; Palladium - chemistry; Stereoisomerism; Synthesis; Synthesis (chemistry); tandem cyclisation; Utilities; lycoranes; Heck reaction; Lewis acids; tandem cyclisation; erythrina

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 (±)‐γ‐lycorane, incorporating a new intramolecul...