Silyl migrations in D-xylose derivatives: total synthesis of a marine quinoline alkaloid.
A versatile method for the synthesis of orthogonally protected D-xylose 1-thioethers is described using unusual silyl group migrations which were pivotal in the synthesis of 4,8-dimethyl-6-O-(2',4'-di-O-methyl-β-D-xylopyranosyl)hydroxyquinoline confirming the structure and absolute configuration of the natural product.
School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.
Anuchit
A
Phanumartwiwath
Thomas W
TW
Hornsby
Joazaizulfazli
J
Jamalis
Christopher D
CD
Bailey
Christine L
CL
Willis
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D014994:Xylose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
C587705:4,8-dimethyl-6-O-(2',4'-di-O-methyl-beta-D-xylopyranosyl)hydroxyquinoline; D000470:Alkaloids; D001688:Biological Products; D006912:Hydroxyquinolines; D012821:Silanes; D014994:Xylose