Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 537-558

  Jiménez, José M ^a   Rifé, Joan ^a   Ortuño, Rosa M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 METHANOHOMOSERINE; 2,3 METHANOMETHIONINE; AMINO ACID; CORONAMIC ACID; CYCLOPROPANE DERIVATIVE; NORCORONAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0038459459     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00038-9     Document Type: Article

References (33)

1. For reviews on the isolation, synthesis, and biological properties of cyclopropane amino acids, see: (a) Stammer, C. H. Tetrahedron 1990, 46, 2234.
2. (b) Alami, A.; Calmes, M.; Daunis, J. Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5.
3. Burgess, K.; Ho, K.-K.; Moye-Sherman D. Synlett 1994, 575.
4. Sakamura, S.; Ichichara, A.; Shiraishi, K.; Sato, H.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636.
5. Mitchell, R. E. Phytochemistry 1985, 24, 1485.
6. Hoffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant PhysioL 1982, 70, 195.
7. Pirrung, M. C.; McGeehan, G. M. J. Org. Chem. 1986, 51, 2103.
8. Previous communications: (a) Jiménez, J. M.; Casas, R.; Ortuño, R. M. Tetrahedron Lett. 1994, 35, 5945.
9. (b) Jiménez, J. M.; Rifé, J.; Ortuño, R. M. Tetrahedron : Asymmetry, 1995, 6, 1849.
10. (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53.
11. (b) Schmidt, U.; Lieberknecht, A.; Kazmaier, U.; Griesser, H.; Jung, G.; Metzger, J. Synthesis 1991, 49.
12. D-glyceraldeyde acetonide is easily prepared from cheap and commercially available D-mannitol, according to: Mann, J.; Partien, N. K.; Thomas, A. J. Chem. Res. (S) 1987, 369, and references therein.
13. A detailed mechanistic study on the photochemical decomposition of these pyrazolines to cyclopropanes is being carried out in our laboratory. Results will be published elsewhere.
14. Dechoux, L.; Doris, E. Tetrahedron Lett. 1994, 35, 2017.
15. Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 1979.
16. Previous asymmetric syntheses of allo-coronamic acid 1: (a) Marco, J. L. Heterocycles 1987, 26, 2579.
17. (b) Alami, A.; Calmes, M.; Daunis, J.; Escale, F.; Jacquier, R.; Roumestant, M.-L.; Viallefont, P. Tetrahedron: Asymmetry 1991, 2, 175.
18. Williams, R. M.; Fegley, G. J. J. Am. Chem. Soc. 1991, 113, 8796. The N-Boc-derivative, but not free amino acid, is described,
19. Groth, U.; Halfbrodt, W.; Schölkopf, U. Liebigs Ann. Chem., 1992, 351.
20. (e) Alcaraz, C.; Herrero, A.; Marco, J. L. Fernández-Alvarez, E.; Bernabé, M. Tetrahedron Lett. 1992, 33, 5605. The synthesis of (+)-allo-coronamic acid is described.
21. (f) Cativiela, C.; Díaz-de-Villegas, M. D.; Jiménez, A. I. Tetrahedron: Asymmetry 1995, 6, 177.
22. Pirrung, M. C.; Dunlap, S. E.; Trinks, U. P. Helv. Chim. Acta 1989, 72, 1301.
23. Aitken, D. J.; Guillaume, D.; Husson H.-P. Tetrahedron 1993, 49, 6375.
24. Asymmetric syntheses of 3: (a) See ref 13.
25. (b) Aitken, D. J.; Royer, J.; Husson, H.-P. J. Org. Chem. 1990, 55, 2814.
26. (a) Malin, D. H.; Payza, K.; Lake, J. R.; Corriere, L. S.; Benson, T. M.; Smith, D. A.; Baugher, R. K.; Ho, K.-K.; Burgess, K. Peptides 1993, 14, 47.
27. (b) Malin, D. H.; Lake, J. R.; Ho, K.-K.; Corriere, L. S.; Garber, T. M.; Waller, M.; Benson, T.; Smith, D. A.; Luu, T.-A.; Burgess, K. Peptides 1993, 14, 731.
28. allo-Norcoronamic acid 2 was obtained for the first time by Baldwin through resolution of the racemic mixture: Baldwin, J. E.; Adlington, R. M.; Rawlings, B. J.; Jones, R. H. Tetrahedron Lett. 1985, 26, 485.
29. Previous asymmetric syntheses of 2: (a) See ref 5.
30. (b) Alami, A.; Calmes, M.; Daunis, J.; Escale, F.; Jacquier, R.; Viallefont, P. Tetrahedron: Asymmetry, 1991, 2, 175.
31. Cativiela, C.; Díaz-de-Villegas, M. D.; Jiménez, A. I. Tetrahedron: Asymmetry, 1995, 6, 2067.
32. For a review on the characteristic reactivity of cyclopropane systems, see: de Meijere, A. Angew. Chem. Int. Ed. Engl. 1979, 18, 809.
33. First asymmetric synthesis of 4 and the other three stereoisomers of 2,3-methanomethionine: Burgess, K.; Ho, K.-K. J. Org. Chem. 1992, 57, 5931.