Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol.
A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF(3)·Et(2)O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
Jing
J
Zeng
Seenuvasan
S
Vedachalam
Shaohua
S
Xiang
Xue-Wei
XW
Liu
D001592:Benzyl Alcohols / Q000138:chemical synthesis*; D001881:Borates / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D017611:Fluorine Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
D001592:Benzyl Alcohols; D001881:Borates; D017611:Fluorine Compounds; D005663:Furans; C456047:varitriol; D005459:Fluorides