Versatile 8-oxabicyclo[3.2.1]oct-6-en-3-one: stereoselective methodology for generating C-glycosides, delta-valerolactones, and polyacetate segments.
[figure: see text] A new rearrangement of functionalized methoxy glycosides and a regioselective as well as stereoselective intramolecular Michael addition giving delta-valerolactones and C-glycosides are described. Applications to the synthesis of marine natural products are reported. Chemoselective deprotection of benzylated hydroxy groups is assumed to be facilitated by 6-endo-tet interaction with the 1,3-dithiane functionality.
Vakalopoulos
A
A
Department of Organic Chemistry, University of Hannover, Schneiderberg 1B, D-30167 Hannover, Germany.
Hoffmann
H M
HM
D000085:Acetates / Q000138:chemical synthesis*; D001685:Biological Factors / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D012623:Seawater
D000085:Acetates; D001685:Biological Factors; D006027:Glycosides; D007202:Indicators and Reagents; D007783:Lactones; C037556:gamma-valerolactone