Synthesis of ï¡-Hydroxy ï¢-Proline: Potential for Organocataly-sis Reactions
Keywords:ï¢-proline, organocatalysis, GABA transporter, Geissman Waiss Lactone
A chiral organic molecule, L-proline catalyzed an enantioselective transformation reaction has becoming interesting synthetic protocol especially in the area of organocatalysis. Herein, a synthetic approach towards ï¡-hydroxy-ï¢-proline starting from bicyclic lactone lactam is hereby described. The syntheses utilized dicarboxylation reaction of bicyclic lacton lactam, followed by ether hydrolysis of the bicyclic ether and oxidation reaction of the primary alcohol. The synthetic strategy disclosed here allows further the enantioselective synthesis of a variety of unnatural amino acids based on ï¢-proline structure.
 Dalko P I, Moisan L (2001), Enantioselective Organocatalysis. Angew. Chem., Int. Ed. 40, 3726.(b) Jarvo E R, Miller S J (2002), Amino Acids and Peptides as Asymmetric Organocatalysts. Tetrahedron 58, 2481.
 Rouhi A M (2004), Traditional methods thrive because numerous hurdles, including tough luck, slow down the commercialization of catalytic processes.Chem. Eng. News 82, 47-62.
 Jeff T S, Derek D S, Carlos F B (2005), Organocatalytic Enantioselective Synthesis of Metabotropic Glutamate Receptor Ligands. Org. Lett. 7, 3885-3888.
 Vogt H,Vanderheiden S & Brase S. (2003), Proline-catalysed asymmetric amination of Î±,Î±-disubstituted aldehydes: synthesis of configurationally stable enantioenriched Î±-aminoaldehydes. Chem.Commun, 2448-2449.
(a) List B (2002), Direct catalytic asymmetric Î±-amination of aldehydes. J. Am. Chem. Soc.124, 5656-5657. (b) Bogevig, A., Juhl, K., umaragurubaran, N., Zhuang, W., Jorgensen, K. A. (2002). Direct Organoâ€Catalytic Asymmetric Î±â€Amination of Aldehydesâ€”A Simple Approach to Optically Active Î±â€Amino Aldehydes, Î±â€Amino Alcohols, and Î±â€Amino Acids. Angew.Chem., Int. Ed 41, 1790-1793.
 Wanner, K. T, (2010). Development of GABA uptake inhibitors, Frontiers in Medicinal Chemistry, Munster, Germany, p. 31.
 Nurbo J, Peterson S D, Daul G, Danidson U H, Karlen A & Sandstrom A (2008), Î²-Amino acid substitutions and structure-based CoMFA modeling of hepatitis C virus NS3 protease inhibitors. Bioorganic & Med. Chem 16, 5990-5605. (a) Jouin P & Castro B J. (1987), Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid. Chem. Soc. Perkin Trans 1, 1177-1181. (b) Ali. M. T. M, Synthesis of (-)-Geissman Waiss Lactone, cis gamma-butyrolactone derivatives and gamma-peptides (eBook), Worldcat, (2012).
 Ali M T M, Macabeo A P G, Wan B, Franzblau S & Reiser O (2013), Asymmetric approach toward new conformationally constrained cis-gamma butyrolactone. In Abstract of papers of the American Chemical Society Vol. 245
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