Otte, F., Schmidt, B.
Matsuda-Heck Arylation of Glycals for the stereoselective Synthesis of Aryl C-Glycosides
J. Org. Chem. 2019, 84, 14816-14829.
DOI: 10.1021/acs.joc.9b02410
Aryl C-glycosides occur as structural patterns in many natural and non-natural bioactive compounds. We devise a novel synthetic strategy that relies on a Heck-type arylation of glycals (in turn synthesized de novo from lactic acid derivatives using olefin metathesis methods) with arene diazonium salts (commonly known as Matsuda-Heck-reaction). The gliflozin derivative shown in the graphical abstract is a representative application example.
Zurück zur Übersicht »