One step synthesis of orthogonally protected diaminodicarboxylic acids by mixed kolbe electrolysis

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 23, 1997, Pages 2963-2966

  Hiebl, Johann ^a,c   Kollmann, Hermann ^b   Rovenszky, Franz ^a   Winkler, Karin ^b  

^a Topcro Pharma Research GmbH   (Austria)

^b Nycomed Holdings AS   (Austria)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 DIAMINOSUBERIC ACID DERIVATIVE; DICARBOXYLIC AMINO ACID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ELECTROLYSIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030721481     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10130-5     Document Type: Article

References (14)

1. Laerum, O. D.; Sletvold, O.; Bjerknes, R.; Eriksen, J. A.; Johansen, J. H.; Schanche, J. S.; Tverteraas, T.; Paukovitz, W. R. Exp. Hematol. 1988, 16, 274-280.
2. Bhatnagar, P. K.; Agner, E. K; Alberts, D.; Arbo, B. E.; Callahan, J. F.; Cuthbertson, A. S.; Engelsen, S. J.; Fjerdingstad, H.; Hartmann, M.; Heerding, D.; Hiebl, J.; Huffman, W. F.; Hysben, M.; King, A. G.; Kremminger, P.; Kwon, C.; LoCastro, S.; Løvhaug, D.; Pelus, L. M.; Petteway, S.; Takata, J. S. J. Med. Chem. 1996, 39, 3814-3819.
3. Cox, R. J.; Sherwin, W. A.; Lam, L. K. P.; Vederas, J. C. J. Am. Chem. Soc. 1996, 118, 7449-7460 and references cited therein.
4. a) Jurgens, A. R. Tetrahedron Lett. 1992, 33, 4727-4730.
5. b) Williams, R. M.; Yuan, C. J. Org. Chem. 1992, 57, 6519-6527.
6. c) Bold, G.; Allmendinger, T.; Herold, P.; Moesch, L.; Schär, H.-P.; Duthaler, R. Helv. Chim. Acta 1992, 75, 865-882.
7. d) Holcomb, R. C.: Schow, S.; Ayral-Kaloustian, S.; Powell, D. Tetrahedron Lett. 1994, 35, 7005-7008.
8. Keller, O. Dissertation, E.T.H. Zürich. 1974.
9. Nutt, R. F; Veber, D. F.; Saperstein, R. J. Am. Chem. Soc. 1980, 102, 6539-6545.
10. Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. J. J. Org. Chem. 1980, 45, 3078-3080.
11. Hiebl, J.; Blanka, M.; Gutman, A.; Kollmann, H.; Leitner, C.; Mayrhofer, G.; Rovenszky, F.; Winkler, K. submitted to Tetrahedron.
12. HOEtTos is available from Loba Feinchemie AG, A-2401-Fischamend, Austria.
13. 2), 5.3(m, 1, NH), 7.2-7.32(m, 12, 10 phenyl-H, 2 tolyl-H), 7.70(d, 2, J = 8.2Hz, 2-tolyl-H).
14. Please note that diaminoadipic acid derivatives are not available by Schöllkopf route according Ref. 4c (footnote 3 on page 868).