The carbonylative cross‐coupling reactions of 2‐iodoglycals with thiols and selenols in the presence of molybdenum hexacarbonyl as a solid source of carbon monoxide is described. This methodology permitted the synthesis of 29 C2‐glycosides bearing thioester and selenoester functionalities in moderate to excellent yields and high functional group tolerance. Moreover, this communication describes the first catalytic carbonylative coupling reaction of selenols with a carbon electrophile.
A mild stereo‐ and regioselective Cu‐catalyzed hydroboration method for the synthesis of (Z)‐seleno‐alkenyl boronates and (Z)‐thio‐alkenylboronates from internal alkynes in the presence of commercially available B2pin2 is presented. This highly selective transformation relies on the use of N‐heterocyclic carbene (NHC) complex IPrCuCl as the active catalytic species. We also explore the functionalization of the alkenylboronates obtained via oxidation to give α‐chalcogeno ketones, useful building blocks for the synthesis of more complex chalcogen‐containing molecules.
The synthesis of amidoglucals and glucal esters in good to high yields using 2-iodo-3,4,6-tri-O-acetyl-d-glucal as a substrate, Mo(CO)6 as a carbon monoxide source and PdCl2 as a catalyst is reported.
The iron(III)‐promoted synthesis of densely‐substituted 4H‐chalcogenchromene from organochalcogen propargylamines in the presence of diaryl dichalcogenides is reported. Subsequent C2‐functionalization with electrophiles and potassium trifluoroborate salts via Suzuki‐Miyaura coupling reaction are also presented. A plausible mechanism based on HRMS experiments is proposed and discussed.
C-Glycosides are valuable organic compounds in the field of medicinal chemistry due to their ubiquity inside living systems and pronounced biological activity. Herein, we describe an approach to alkyl-ketones bearing glycal units via the Pd- [a]
The synthesis of C‐glycosides is of great importance in the field of carbohydrate chemistry given its ubiquity in biologically active molecules. Herein, we describe a protocol for the Pd‐catalyzed carbonylative Heck reaction of activated olefins and 2‐iodoglycals. A variety of α,β‐unsaturated 2‐ketoglycosides were obtained in up to 89 % yield using d‐glucal, d‐galactal, d‐xylal, and l‐arabinal derivatives.
Because of the increased resistance to currently available antifungals, fungal infections represent a significant challenge to human health. Herein, we report the synthesis of 2-aryloxazoline derivatives from the reaction between L-threonine and derivatives of salicylic or naphthoic acid. In total, 26 compounds were obtained and tested against species of Candida, Cryptococcus, and Aspergillus. We found that all of the compounds inhibited the growth of Candida species at low concentrations (<0.25 μg/mL) and exhibited reduced hemolytic and cytotoxic activities. Additionally, compounds 4i and 9i were especially effective against antifungalresistant isolates and the emerging fungus Candida auris. However, the compounds were less active on Cryptococcus and Aspergillus. Because of the improved in vitro antifungal efficacy and attenuated cytotoxicity, these two 2-aryloxazolines obtained from salicylic and naphthoic acid derivatives, respectively, may be considered lead molecules for the development of novel antifungal drugs.
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