Short Total Synthesis of (±)‐γ‐Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction. Issue 20 (20th March 2017)

• Record Type: Journal Article
• Authors: Monaco, Alessandra; Szulc, Blanka R.; Rao, Zenobia X.; Barniol‐Xicota, Marta; Sehailia, Moussa; Borges, Bruno M. A.; Hilton, Stephen T.
• Is Part Of: Chemistry. Volume 23:Issue 20(2017)
• Page Start: 4750
• Page End: 4755
• Publication Date: 2017-03-20
• Subjects: erythrina -- Heck reaction -- Lewis acids -- lycoranes -- tandem cyclisation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201700143
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield. Abstract : Tandem cyclisation : The pentacyclic structure of the natural product (±)‐γ‐lycorane was synthesized by a new sequential Lewis acid mediated intramolecular acylal cyclisation (IAC)/Heck coupling approach. By using this methodology, a range of bicyclic heterocycles was also synthesized in good yields demonstrating the potential of the IAC reaction to access complex heterocycles (see scheme).