676268-52-3Relevant academic research and scientific papers
Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling
Freas, Dylan J.,Fu, Gregory C.,Yang, Ze-Peng
, p. 8614 - 8618 (2021/06/28)
Interest in unnatural α-Amino acids has increased rapidly in recent years in areas ranging from protein design to medicinal chemistry to materials science. Consequently, the development of efficient, versatile, and straightforward methods for their enanti
Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximes.
Cooper, Tracey S,Laurent, Pierre,Moody, Christopher J,Takle, Andrew K
, p. 265 - 276 (2007/10/03)
A new asymmetric synthesis of alpha-amino acids is described in which the key step is the highly diastereoselective addition of organolithium carboxyl synthons (2-furyllithium, phenyllithium, vinyllithium) to (R)- and (S)-O-(1-phenylbutyl) oximes to give hydroxylamines, with vinyllithium being the most satisfactory nucleophilic reagent. Subsequent reductive cleavage of the N-O bond in hydroxylamines, followed by N-protection, and oxidative cleavage of the carboxyl precursor gave a range of N-protected amino acids and esters. The method was exemplified by the synthesis of a range of derivatives of non-proteinogenic amino acids such as 4-bromophenylalanine, tert-leucine, norvaline, cyclohexyl- and aryl-glycines, 2-amino-8-oxodecanoic acid (Aoda) and alpha-methylvaline.
Synthesis of (S)-2-amino-8-oxodecanoic acid (Aoda) and apicidin A
Mou, Liyuan,Singh, Gurdial
, p. 6603 - 6606 (2007/10/03)
The synthesis of (S)-2-amino-8-oxodecanoic acid, a constituent of the cyclic tetrapeptides, the apicidins, was accomplished under photolytic conditions in the presence of tri-n-butyltin hydride using glutamic acid. This enabled a total synthesis of apicidin A to be completed.
