Asymmetric Synthesis of .gamma.-D- and -L-Glutamyl-L-meso-diaminopimelic Acid Dipeptide

The Facile Production of N-Methyl Amino Acids via Oxazolidinones

“…These include methods for direct methylation, 1-5 reductive amination, 6-12 alternative methods [13][14][15][16][17][18] and through the generation of oxazolidinones and their subsequent transformation to the N-methyl (alkyl) product. [19][20][21][22][23] In addition, there are strategies involving the use of immonium ions in Diels-Alder/retro-Diels-Alder sequences, 24 the nucleophilic displacement of triflates, 25 the hydroxyamination of chiral enolates 26 and the Mitsunobu reaction. 27 Some of these methods suffer from limitations in the range of amino acids to which they are applicable, some utilize rather long synthetic sequences and some cause at least partial racemisation of the substrate.…”

“…The work described in this paper exploits the oxazolidinone route [19][20][21][22][23] to generate a range of N-methyl amino acids by using simple reproducible chemistry. The reaction plan presented in this paper is depicted by the general diagram in Fig.…”

Synthesis of N‐Alkyl Amino Acids

“…These conversions did not produce N-methyl amino acids, but instead the methylene carbon was cleaved entirely from the lactone substrate, providing the parent amino acids. Williams and Yuan [79] also observed this result.…”

Natural Products Synthesis: Enabling Tools To Penetrate Nature’s Secrets of Biogenesis and Biomechanism

“…We have utilized the chiral glycine methodology to synthesize a variety of natural products including: β-carboxyaspartic acid, 55 (+)-6-hydroxymethyl-2,6- diaminopimelic acid, 56 (−)-cucurbitine, 57 norcoronamic acid, 58 coronamic acid, 58 2,6-diaminopimelic acid, 59 statine, 60 γ–D(L)- glutamyl-L- meso- diaminopimelic acid dipeptide, 61 (−)- spirotryprostatin B, 62 (−)-spirotryprostatin A, 63 (−)-tetrazomine, 64 ( 2S,3R )-capreomycidine, 65 capreomycin IB, 66 ( S )-(+)-carnitine, 67 ( R )-(−)-carnitine, 68 hypusine, 69 negamycin, 70 renieramycin G, 71 jourumycin, 71 cylindrospermopsin, 72 7- epi- cyclindrospermopsin, 73 and 7-deoxycylindrospermopsin. 74 …”