Sharpless asymmetric dihydroxylation of 5-aryl-2-vinylfurans: application to the synthesis of the spiroketal moiety of papulacandin D.
[formula: see text] Using the Sharpless catalytic asymmetric dihydroxylation reaction on 5-aryl-2-vinylfurans, diols are produced in high enantioexcess. The resulting diols can be efficiently transformed into the spiroketal ring precursor of the antifungal compound papulacandin D. Stereoselective reduction of this precursor followed by a diastereoselective dihydroxylation completes the synthesis of a mannopyranoside isomer of a papulacandin derivative.
Balachari
D
D
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
O'Doherty
G A
GA
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D054714:Echinocandins; D005663:Furans; D006900:Hydroxylation; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D014753:Vinyl Compounds
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D054714:Echinocandins; D005663:Furans; D007202:Indicators and Reagents; D014753:Vinyl Compounds; C014732:papulacandins