A novel strategy towards the asymmetric synthesis of orthogonally funtionalised 2-N-benzyl-N-α-methylbenzyl-amino-5-carboxymethyl- cyclopentane-1-carboxylic acid

Molecules

Volumn 9, Issue 5, 2004, Pages 373-382

  Garrido, Narciso M ^a   El Hammoumi, Mohamed M ^a   Díez, David ^a   García, Mercedes ^a   Urones, Julio G ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Aminodiester orthogonal protection; Asymmetric synthesis; Chiral lithium amide; Domino reaction; amino acids; aminocyclopentane carboxilate

Indexed keywords

2 N BENZYL N ALPHA METHYLBENZYLAMINO 5 CARBOXYMETHYLCYCLOPENTANE 1 CARBOXYLATE; 2 N BENZYL N ALPHA METHYLBENZYLAMINO 5 CARBOXYMETHYLCYCLOPENTANE 1 CARBOXYLIC ACID; 2 N BENZYL N ALPHA METHYLBENZYLAMINO 5 METHOXYCARBONYLMETHYLCYCLOPENTANE 1 CARBOXYLATE; 2 N BENZYL N ALPHA METHYLBENZYLAMINO 5 METHOXYCARBONYLMETHYLCYCLOPENTANE 1 CARBOXYLIC ACID; 2 N BENZYL N ALPHA METHYLBENZYLAMINO 5 TERT BUTOXYCARBONYMETHYLCYCLOPENTANE 1 CARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; LITHIUM; TERT BUTYL 2 N BENZYL ALPHA METHYLBENZYLAMINO 5 METHOXYCARBONYLMETHYLCYCLOPENTANE 1 CARBOXYLATE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DRUG SYNTHESIS; HYDROLYSIS; MICHAEL ADDITION;

EID: 3242877439     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/90500373     Document Type: Article

References (14)

1. Martinek, T.A.; Táth, G.K.; Vass, E.; Hollósi, M.; Fülop, F. cis-2-Aminocyclopentanecarboxylic acid oligomers adopt a sheetlike structure: switch form helix to nonpolar strand. Angew. Chem. Int. Ed. Engl. 2002, 41, 1718-1721.
2. Appella, D.H.; Christianson, L.A.; Klein, D.A.; Powell, D.R.; Huang, X.; Barchi, J.J.; Gellman, S.H. Residue-based control of helix shape in beta-peptide oligomers. Nature 1997, 387, 381-384.
3. Appella, D.H.; Christianson, L.A.; Klein, D.A.; Richards, M.R.; Powell, D.R.; Gellman, S.H. Synthesis and structural characterization of helix-forming beta-peptides: trans-2-aminocyclo-pentanecarboxylic acid oligomers. J. Am. Chem. Soc. 1999, 121, 7574-7581.
4. Barchi Jr, J.J.; Huang, X.; Appella, D.H.; Christianson, L.A.; Durell, S.R.; Gellman, S.H. Solution conformations of helix-forming beta-amino acid homooligomers J. Am. Chem. Soc. 2000, 122, 2711-2718.
5. Cheng, R.P.; Gellman, S.H.; DeGrado, W.F. β-Peptides: From structure to function. Chem. Rev. 2001, 101, 3219-3232 and references cited therein.
6. Porter, E.A.; Wang, X.; Schmitt, M.A.; Gellman, S.H. Synthesis and 12-Helical Secondary Structure of β-Peptides Containing (2R,3R)-Aminoproline. Org. Lett. 2002, 4, 3317-3319.
7. Porter, E.A.; Wang, X.; Lee, H.S.; Wisblum, B.; Gellman, S.H. Non-haemolytic β-amino-acid oligomers. Nature 2000, 565-565.
8. Woll, M.G.; Fisk, J.D.; LePlae, P.R.; Gellman, S.H. Stereoselective synthesis of 3-substituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into short 12-helical β-peptides that fold in water. J. Am. Chem. Soc. 2002, 124, 12447-12452.
9. Urones, J.G.; Garrido, N.M.; Díez, D.; El Hammoumi, M.M.; Dominguez, S.H.; Casaseca, J.A.; Davies, S.G.; Smith, A.D. Asymmetric synthesis of the stereoisomers of 2-amino-5-carboxymethyl-cyclopentane-1-carboxylate. Org. Biomol. Chem. 2004, 2, 364-372.
10. Scheffer, J.R.; Wostradowski, R.A. Solution Photochemistry. X. A study of the effects of double-bond geometry and of increasing double-bond separation on the photochemical reactions of acyclic nonconjugated dienes. J. Org. Chem. 1972, 37, 4317-4324.
11. Aurell, M.J.; Gil, S.; Mestres, R.; Parra, M.; Tortajada, A. Acerca del mecanismo radicalario del acoplamiento oxidativo de dianiones de ácidos carboxílicos. Competición entre sustitución nucleofílica y transferencia electrónica. An. Quim. 1994, 90, 457-466.
12. Aurell, M.J.; Gil, S.; Parra, M.; Tortajada, A.; Mestres, R. Iodine oxidative coupling of diene and triene-diolates of unsaturated carboxylic acids Tetrahedron 1991, 47, 1997-2004.
13. Aurell, M.J.; Gil, S.; Tortajada, A.; Mestres, R. A facile synthesis of 2,6-octadienedioic and 2,4,8,10-dodecatetraenedioic acids by oxidative coupling of 2-butenoic or 2,4-hexadienoic acids. Synthesis 1990, 317-319.
14. Aurell, M.J.; Gil, S.; Tortajada, A.; Mestres, R.; García-Raso, A. Silver ion oxidative coupling of diene and triene-diolates of unsaturated carboxylic acids. A facile synthesis of octa- and dodeca-dienedioic acids. Tetrahedron Lett. 1988, 29, 6181-6182.