Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision

This study describes the first asymmetric total synthesis of the proposed structure of the archaeal membrane-spanning tetraether lipid crenarchaeol. The synthetic material was compared by NMR and GC-MS analysis with natural crenarchaeol. Detailed NMR analysis ultimately enabled the structure revision of crenarchaeol, identifying one out of 22 sterecenters to be inverted.