Total synthesis of isokidamycin.
The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O→C-glycoside rearrangement.
O'Keefe
B Michael
BM
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Mans
Douglas M
DM
Kaelin
David E
DE
Martin
Stephen F
SF
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
D000617:Aminoglycosides; C100062:kidamycin