Putative biosynthetic cycloadditions en route to the diterpenoid (+)-chatancin

• DOI: 10.1016/j.tet.2016.11.031
• Publication Date: 2016-11-14T18:20:44Z
• Authors: Stephanie R. Hare; Jessica M. Farnham; Dean J. Tantillo
• Keywords: Furan

Abstract Density functional theory calculations were carried out in order to determine the viability of putative mechanistic pathways for formation of the diterpenoid (+)-chatancin. It was found that a cycloaddition involving a pyrylium ion would have a lower energetic barrier than previously proposed cycloadditions involving a 2H-pyran or furan. All three reactions are predicted to be concerted.