Diene(tricarbonyl)iron complexes linked to spirooxazolones for the synthesis of cyclopropyldihydroxyphenylalanine

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5393-5395

  Schumacher, Marc ^a   Miesch, Laurence ^a   Franck Neumann, Michel ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Cyclopropyldihydroxyphenylalanine; Diazomethane; Diene(tricarbonyl)iron complexes; Hydrazine; Oxazolones; Spiroazlactones

Indexed keywords

ALKADIENE; CYCLOPROPYL 3,4 DIHYDROXYPHENYLALANINE; DIAZOMETHANE; ESTER DERIVATIVE; IRON COMPLEX; LACTONE; OXAZOLONE; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; CYCLOADDITION; CYCLOPROPANATION; DRUG SYNTHESIS; HYDROLYSIS; RING CLOSING METATHESIS; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

EID: 0037525647     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01312-1     Document Type: Article

References (16)

1. Goodman M., Shao H. Pure Appl. Chem. 68:1996;1303.
2. Awad W.I., Fateen A.K., Zayed M.A. Tetrahedron. 20:1964;891.
3. Bernabe M., Arenal I., Cuevas O., Fernandez-Alvarez E. Tetrahedron. 39:1983;1387.
4. Hines J.W. Jr., Breitholle E.G., Sato M., Stammer C.H. J. Org. Chem. 41:1976;1466.
5. Suzuki M., Kumar S.D., Stammer C.H. J. Org. Chem. 48:1983;4769.
6. Bernabe M., Cuevas O., Fernandez-Alvarez E. Eur. J. Med. Chem. 14:1979;33.
7. Sheehan J.C., Hlavka J.J. J. Org. Chem. 21:1956;439.
8. Erlenmeyer E. Ann. 275:1893;1.
9. Plöchl J. Ber. 17:1884;1616.
10. Buck, J. S.; Ide, W. S. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p. 55.
11. Stammer C.H. Tetrahedron. 46:1990;2231.
12. Methanolysis of the mixture of 9 and 10 led to easily separable amide.
13. McGreer D.E., Wu W.S. Can. J. Chem. 45:1967;461.
14. Van Auken T.K., Rinehart K.L. Jr. J. Am. Chem. Soc. 84:1962;3736.
15. Burk M.J., Allen J.G. J. Org. Chem. 62:1997;7054.
16. 3, 75 MHz): δ 19.1, 58.7, 58.7, 82.0, 87.8, 172.1, 210.4.