7370-92-5Relevant articles and documents
Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- And 5-acetoxyalkanethioamide analogues
Shimotori, Yasutaka,Hoshi, Masayuki,Ogawa, Narihito,Miyakoshi, Tetsuo,Kanamoto, Taisei
, p. 84 - 98 (2020/07/03)
5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.
Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan
Hsu,Fang
, p. 8573 - 8584 (2007/10/03)
By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.
Lipase-catalysed Baeyer-Villiger Reactions
Lemoult, Stephanie C.,Richardson, Paul F.,Roberts, Stanley M.
, p. 89 - 92 (2007/10/02)
The Baeyer-Villiger Oxidation of some 2- and 3-substituted cyclopentanones and cyclohexanones using myristic acid and hydrogen peroxide is catalysed by Candida anatarctica lipase.