Asymmetric synthesis of 3-alkyl pipecolic acids

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3699-3700

  Zaparucha, A ^a   Danjoux, M ^a   Chiaroni, A ^a   Royer, J ^a   Husson, H P ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYANO 6 PHENYLOXAZOLOPIPERIDINE; 4 PHENYL 3,4,7,8 TETRAHYDRO 6H PYRIDO (2,1 C)(1,4)OXAZIN 1 ONE; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; ENZYME INHIBITION; IMMUNOREGULATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033532107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00591-2     Document Type: Article

References (11)

1. [1] Zabriskie TM, Kelly WL and Liang X. J. Am. Chem. Soc. 1997;119 : 6446-6447 and references cited therein.
2. [2] Copelend TD, Wondrak EM, Toszer J, Roberts MM, Oraszlan S. Biochem. Biophys. Res. Commun..1990; 169 : 310-314.
3. [3] Dragovich PS, Parker JE, French J, Incacuan M, Kalish VJ, Kissinger CR, Knighton DR, Lewis CT, Moomaw EW, Parge HE, Pelltier LAK, Prins TJ, Showalter RE, Tatlock JH, Tucker KD, Villafranca JE. J. Med. Chem. 1996;39: 1872-1884.
4. [4] Gillard J, Abraham A, Anderson PC, Beaulieu PL, Bogri T, Bousquet Y, Grenier L, Guse Y, Lavallée P. J. Org. Chem. 1996; 61: 2226-2231.
5. [5] Ho B and Zabriskie TM. Bioorg. Med. Chem. Lett. 1998; 8: 739-744.
6. [6] Skiles JW, Giannousis PP, Fales KR, Bioorg. Med. Chem. Lett. 1996; 6: 963-966.
7. [7] Berrien J-F, Royer J and Husson H-P. J. Org. Chem. 1994; 59: 3769-3774.
8. [8] Toyooka N, Tanaka K, Momose T, Daly WJ and Garraffo HM. Tetrahedron 1997; 53: 9553-9574.
9. 4. Distillation of the solvents under reduced pressure afforded the crude product which was purified by flash chromatography on silica gel (eluant cyclohexane/diethyl ether).
10. [10] Atomic coordinates have been deposited with the Cambridge Crystallographic Center.
11. 3) δ: 13.1, 22.9, 29.9, 35.7, 44.7, 63.4, 170.0 This compound has been previously described in racemic form: Shuman RT, Ornstein PL, Paschal JW, Gesellchen PD J. Org. Chem. 1990; 55: 738-741.