Natural products demand highest dedication of our synthetic, medicinal, and analytical chemists.
We consider the chemistry of complex natural products to be an inspiration for design and synthesis in the discovery stage of projects.
Natural strigol is a plant hormone that induces the germination of parasitic weeds. In a long-standing collaboration with the Radboud University of Nijmegen, Mercachem has worked on the synthetic exploration of strigolactones. The complexity of the compounds has resulted in many ambiguous and corrected strigolactone structures in the literature.
In a recent publication, we secured the absolute configurations of two important strigolactone key structures: 5-deoxystrigol (1) and orobanchol (2).
For 5-deoxystrigol, four isomeric analogues were synthesized and subjected to detailed analysis. X-ray crystal diffraction and comparison of reported melting points led to the assignment of the correct structure and configuration of natural orobanchol.
Resynthesis of orobanchol and efficient separation of the isomers by preparative chromatography and recrystallization was achieved. Detailed analysis and X-ray crystallography resulted in unambiguous structural assignments.
Needless to say, we took the opportunity to optimize the synthesis of these compounds and produced ample material for use in downstream biology.
The reported assignments of structures and absolute configurations aid in the understanding of the biological processes of strigolactones.