Organic Chemistry

Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision

Abstract

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.

Content

Thumbnail image of Manuscript_crenarchaeol_final_ChemRxiv.pdf

Supplementary material

Thumbnail image of Supporting Information HRMS spectra Appendix.pdf
Supporting Information HRMS spectra Appendix
Thumbnail image of Supporting Information NMR spectra Appendix.pdf
Supporting Information NMR spectra Appendix
Thumbnail image of Supporting Information Procedures.pdf
Supporting Information Procedures