479411-08-0Relevant academic research and scientific papers
Asymmetric synthesis of (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives
Koulocheri, Sofia D,Magiatis, Prokopios,Skaltsounis, Alexios-Leandros,Haroutounian, Serkos A
, p. 6665 - 6671 (2007/10/03)
A practical synthetic scheme that incorporates an amide functionality into the rigid framework of (2S,3R)-3-hydroxypipecolic acid to produce novel hydroxylated δ-lactam derivatives is reported. The reaction sequence includes the transformation of chiral furanylazide to a 2S-hydroxymethyldihydro pyridone, which was reduced diasteroselectively, protected and oxidized to two corresponding δ-lactam derivatives. Asymmetric dihydroxylation and oxidation of the latter compounds afforded two chiral (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives.
Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived β-hydroxy-α-amino acids: Applications to the total synthesis of carbacephem antibiotic loracarbef
Jackson, Billy G.,Pedersen, Steve W.,Fisher, Jack W.,Misner, Jerry W.,Gardner, John P.,Staszak, Michael A.,Doecke, Christopher,Rizzo, John,Aikins, James,Farkas, Eugene,Trinkle, Kristina L.,Vicenzi, Jeffrey,Reinhard, Matt,Kroeff, Eugene P.,Higginbotham, Chris A.,Gazak,Zhang, Tony Y.
, p. 5667 - 5677 (2007/10/03)
Serine hydroxymethyltransferase (SHMT) derived from recombinant E. coli was found to be able to catalyze the condensation between glycine and 4-pentenaldehyde, affording enantiopure L-erythro-2-amino-3-hydroxy-6-heptenoic acid (AHHA) in high yield and throughput. Conversion of this chiral intermediate of biosynthetic origin to the oral carbacephalosporin antibiotic loracarbef (Lorabid) via β-lactam forming reactions and subsequent Dieckmann cyclization was achieved. (C) 2000 Elsevier Science Ltd.
