Enantioselective synthesis of the papulacandin ring system: conversion of the mannose diastereoisomer into a glucose stereoisomer.
[structure] An enantioselective synthesis of three diastereoisomers of the C-arylglycoside tricyclic spiroketal nucleus of the papulacandins has been achieved, in which the initial asymmetry was introduced via a Sharpless dihydroxylation of substituted 5-aryl-2-vinylfurans. A selective oxidation-reduction sequence converted the mannose isomer into the glucose isomer. This sequence can conveniently produce both the papulacandin ring system along with its enantiomer and diastereomers in only 10-14 steps from 3,5-dimethoxybenzyl alcohol in 5-8% overall yield.
Balachari
D
D
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 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; D005947:Glucose / Q000737:chemistry*; D006900:Hydroxylation; D008358:Mannose / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D054714:Echinocandins; C014732:papulacandins; D005947:Glucose; D008358:Mannose