Synthesis of 5-substituted pipecolic acid derivatives as new conformationally constrained ornithine and arginine analogues

作者: Laurent Le Corre , Hamid Dhimane

DOI: 10.1016/J.TETLET.2005.09.008

关键词:

摘要: Two, orthogonally protected, constrained analogues of arginine have been synthesised in a diastereodivergent manner. The key step involved an electrophilic or radical functionalisation methyl N-Boc-5,6-dehydropipecolate.

参考文章(35)
Zhenyu Zhang, Arthur Van Aerschot, Chris Hendrix, Roger Busson, Frank David, Pat Sandra, Piet Herdewijn, Synthesis of Alanine and Proline Amino Acids with Amino or Guanidinium Substitution on the Side Chain Tetrahedron. ,vol. 56, pp. 2513- 2522 ,(2000) , 10.1016/S0040-4020(00)00123-X
Mark Plehiers, Claude Hootelé, Hydroboration of enecarbamates and the synthesis of β-hydroxypiperidine alkaloids Tetrahedron Letters. ,vol. 34, pp. 7569- 7570 ,(1993) , 10.1016/S0040-4039(00)60402-1
Josyula V.B Kanth, Herbert C Brown, Unusual rapid hydroboration of alkenes using diborane in chlorohydrocarbon solvents Tetrahedron Letters. ,vol. 41, pp. 9361- 9364 ,(2000) , 10.1016/S0040-4039(00)01320-4
Paul L. Ornstein, M.Brian Arnold, William H.W. Lunn, Lawrence J. Heinz, J.David Leander, David Lodge, Darryle D. Schoepp, Heteroatom-substitution as a strategy for increasing the potency of competitive NMDA antagonists Bioorganic & Medicinal Chemistry Letters. ,vol. 8, pp. 389- 394 ,(1998) , 10.1016/S0960-894X(98)00038-9
Makoto Tamaki, Guoxia Han, Victor J. Hruby, Practical and efficient synthesis of orthogonally protected constrained 4-guanidinoprolines. Journal of Organic Chemistry. ,vol. 66, pp. 1038- 1042 ,(2001) , 10.1021/JO005626M
Ding-Guo Liu, Yang Gao, Xiangzhu Wang, James A. Kelley, Terrence R. Burke, Enantioselective synthesis of Nα-Fmoc protected (2S, 3R)-3-phenylpipecolic acid. A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis Journal of Organic Chemistry. ,vol. 67, pp. 1448- 1452 ,(2002) , 10.1021/JO010124+
Manuel Friedel, Thomas Lindel, Synthesis of l-aminohomohistidine (l-Ahh) Tetrahedron Letters. ,vol. 45, pp. 2779- 2781 ,(2004) , 10.1016/J.TETLET.2004.02.027
Marta R.P Norton Matos, Carlos A.M Afonso, Robert A Batey, Synthesis of 3-aminopyrrolidines and piperidines from endocyclic enamine derivatives Tetrahedron Letters. ,vol. 42, pp. 7007- 7010 ,(2001) , 10.1016/S0040-4039(01)01433-2