A fully synthetic route to the papulacandins. Stereo-specific spiroacetalization of a C-1-arylated methyl glycoside.
Lewis acid-catalyzed, hetero Diels-Alder reaction of (E)-1-methoxy-3-trimethylsilyloxy-1,3-butadiene with 6-benzoyloxymethyl-2,4-dibenzyloxy benzaldehyde afforded 2-(6-benzoyloxymethyl-2,4-dibenzyloxyphenyl)-2,3-dihydro-4H- pyran-4-one. This was converted into a derivative of papulacandin D by a stereo-specific, spiroacetalization of a C-1 methoxylated aryl glycoside, [3,5-dibenzoyloxy-(methyl 3-O-acetyl-4,6-di-O-benzoyl-DL-glucopyranosid-1-yl)phenyl]methyl benzoate.
Danishefsky
S
S
Department of Chemistry, Yale University, New Haven, Connecticut 06511.
Phillips
G
G
Ciufolini
M
M
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D054714:Echinocandins; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D054714:Echinocandins; D007202:Indicators and Reagents; C014732:papulacandins