Chalcogeno−Morita−Baylis−Hillman Reaction of Enones with Acetals: Simple α-Alkoxyalkylation of Enones

1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1) and the seleno congener (2) reacted with acetals 3 and 21 in the presence of BF3·Et2O to give α-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO3 solution instead of Et3N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave α-(β-hydroxyethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18

Chalcogeno−Morita−Baylis−Hillman Reaction of Enones with Acetals: Simple α-Alkoxyalkylation of Enones

1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1) and the seleno congener (2) reacted with acetals 3 and 21 in the presence of BF3·Et2O to give α-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO3 solution instead of Et3N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave α-(β-hydroxyethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18

Water-Soluble Pleuromutilin Derivative with Excellent in Vitro and in Vivo Antibacterial Activity against Gram-Positive Pathogens

Although earlier pleuromutilin analogues showed potent in vitro antibacterial activity against some Gram-positive pathogens, their in vivo efficacy was low because of insufficient pharmacokinetic properties. We designed novel thioether pleuromutilin derivatives having a purine ring as a polar and water solubilizing group and identified a promising pleuromutilin analogue 6 with good solubility in water (∼50 mg/mL). Compound 6 exhibited excellent in vitro and in vivo antibacterial activity against some Gram-positive strains, including drug-resistant pathogens