Synonyms:111722-89-5;METHYL 2-(PHENYLSULFANYL)HEXADECANOATE;DTXSID50550707
The research focuses on the synthesis of optically active Litsenolide C, a natural product with significant bioactivity, derived from the Lauraceae family. The purpose of the study was to develop a new synthetic strategy that would establish the required absolute configuration at C(3) and C(4) of 3-hydroxy-4-valerolactone through diastereoface differentiation reaction of acrylate α-anion equivalent with (R)-(+)-2-tert-butyldimethylsilyloxypropanal (1), and to form the C(2)-C(3) bond by erythro selective reaction of the aldehyde with lithium enolate derived from 2-(phenylthio)ester. The key chemicals used in the process included methyl 2-(phenylthio)hexadecanoate, (R)-(+)-2-tert-butyldimethylsilyloxypropanal, lithium diisopropylamide (LDA), diethylaluminum chloride, and m-chloroperbenzoic acid. The conclusions of the research were that the synthesis of Litsenolide C was successfully achieved with a yield of approximately 40% based on the aldehyde 1, and the method demonstrated high chemical yield, a specific erythro/threo ratio for the formed C-C bond, and non-chelation-controlled stereoselectivity in the diastereoface differentiation reaction.
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