A straightforward approach towards substituted cis hydroxyprolines

Synlett

Volumn , Issue 7, 2000, Pages 1004-1006

  Mues, Heike ^a   Kazmaier, Uli ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Amino acids; Claisen rearrangements; Iodolactonization; Peptides; Proline

Indexed keywords

HYDROXYPROLINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION;

EID: 0033940819     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

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16. 4 and the solvent was evaporated under reduced pressure. The crude product was purified by crystallization. Therefore the residue was dissolved in ether, 0.85 equiv of (S)-phenethylamine were added, and the solution was stored in the fridge overnight. The precipitated crystals obtained were enantiomerically and diastereomerically pure.
17. A1), 138.37 (C-4), 155.67 (q, J = 36.8 Hz, C-7), 174.09 (C-1).
18. 4): δ = 4.4 (C-5), 14.2 (C-6), 43.7 (C-3), 57.6 (C-2), 82.5 (C-4), 117.2 (q, J = 278.6 Hz, C-8), 159.2 (q, J = 37.7 Hz, C-7), 173.2 (C-1).
19. For comparable iodolactonizations see: Bartlett, P.A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Kitagawa, O.; Sato, T.; Taguchi, T. Chem Lett. 1991, 177. Kazmaier, U. Tetrahedron 1994, 50, 12895.
20. For comparable iodolactonizations see: Bartlett, P.A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Kitagawa, O.; Sato, T.; Taguchi, T. Chem Lett. 1991, 177. Kazmaier, U. Tetrahedron 1994, 50, 12895.
21. For comparable iodolactonizations see: Bartlett, P.A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Kitagawa, O.; Sato, T.; Taguchi, T. Chem Lett. 1991, 177. Kazmaier, U. Tetrahedron 1994, 50, 12895.
22. For comparable iodolactonizations see: Bartlett, P.A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933. Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041. Kitagawa, O.; Sato, T.; Taguchi, T. Chem Lett. 1991, 177. Kazmaier, U. Tetrahedron 1994, 50, 12895.
23. 3): δ = 8.68*, 8.89 (C-6), 43.00*, 45.06 (C-3), 51.56*, 51.61 (C-5), 61.61, 62.71* (C-2), 81.02, 82.19* (C-4), 115.63 (q, J = 286.6 Hz, C-8), 154.03 (q, J = 46.2 Hz, C-7), 170.15, 170.28* (C-1).
24. Related unsubstituted bicyclic lactones (R = H) can also be obtained from trans hydroxyproline: Patchett, A. A.; Witkop, B. J. Am. Chem. Soc. 1957, 79, 185. Papaioannou, D.; Stavropolous, G.; Karagiannis, K.; Francis, G. W.; Brekke, T.; Aksnes, D. W. Acta Chem. Scand. 1990, 44, 243.
25. Related unsubstituted bicyclic lactones (R = H) can also be obtained from trans hydroxyproline: Patchett, A. A.; Witkop, B. J. Am. Chem. Soc. 1957, 79, 185. Papaioannou, D.; Stavropolous, G.; Karagiannis, K.; Francis, G. W.; Brekke, T.; Aksnes, D. W. Acta Chem. Scand. 1990, 44, 243.
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27. A1), 156.55 (q, J = 37.8 Hz, C-7), 170.00 (C-1).
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