Umpolung strategy for the synthesis of 2-deoxy-C-aryl glycosides: a serendipitous, efficient route for C-furanoside analogues.
[reaction: see text] 2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz., C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.
Vijayasaradhi
S
S
Department of Chemistry, Indian Institute of Technology, Madras, Chennai-600 036, India.
Aidhen
Indrapal Singh
IS
D000447:Aldehydes; D000478:Alkylation; D005663:Furans / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
D000447:Aldehydes; D005663:Furans; D006027:Glycosides; D007202:Indicators and Reagents