Synthesis and crystal structure of (±)-Goniotamirenone C

Abstract

The structure of the racemic version of the natural product Goniotamirenone C [racemic anti-6-(2-chloro-1-hydroxy-2-phenylethyl)-2H-pyran-2-one, C13H11ClO3] at 150 K is reported. The compound crystallizes with monoclinic (P21/n) symmetry and with Z′ = 2. One independent molecule is ordered while the other independent molecule exhibits an interesting whole-molecule enantiomeric disorder with occupancies of 0.846 (4) and 0.154 (4). The independent molecules are hydrogen bonded with –OH...O=C linkages into chains that run parallel to the a axis. This structural analysis corrects our previous assignment as the syn isomer [Meesakul et al. (2020). Phytochemistry, 171, 112248–112255].

Keywords

• crystal structure
• goniotamirenone c
• natural product
• semi-synthesis
• chlorohydrin