Synthesis of all four isomers of (E)-4,5-dihydroxydec-2-enal using osmium-catalysed asymmetric dihydroxylation

Tetrahedron Asymmetry

Volumn 8, Issue 8, 1997, Pages 1315-1325

  Allevi, Pietro ^a   Tarocco, Giorgio ^a   Longo, Alessandra ^a   Anastasia, Mario ^a   Cajone, Francesco ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031000574     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00125-0     Document Type: Article

References (21)

1. Benedetti, A.; Comporti, M.; Fulceri, R.; Esterbauer, H. Biochem. Biophys. Acta, 1984, 792, 172.
2. Esterbauer, H.; Zollner, H.; Schaur, R.J. Membrane Lipid Oxidation; Vigo-Pelfrey, C.; Boca Raton, FL: CRC Press; 1990; Vol 1, 239.
3. Esterbauer, H.; Schaur, R.J.; Zollner, H. Free Radical Biol. and Med., 1991, 11, 81.
4. Allevi, P.; Cajone, F.; Ciuffreda, P.; Anastasia, M. Tetrahedron Lett., 1995, 36, 1347.
5. Allevi, P.; Ciuffreda, P.; Tarocco, G.; Anastasia, M. Tetrahedron: Asymmetry, 1995, 6, 2357.
6. For a recent review on the asymmetric dihydroxylation see: (a) Becker, H.; Soler, M.A.; Sharpless, K.B. Tetrahedron, 1995, 51, 1345.
7. (b) Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev., 1994, 94, 2483.
8. Ko, S.Y.; Lerpiniere, J. Tetrahedron Lett., 1995, 36, 2101.
9. (b) Ko, S.Y.; Malik, M.; Dickinson, A.F. J. Org. Chem., 1994, 59, 2570.
10. Kim, B.M.; Sharpless, K.B. Tetrahedron Lett., 1989, 30, 655.
11. (b) Gao, Y.; Sharpless, K.B. J. Am. Chem. Soc., 1988, 110, 7538.
12. Becker, H.; Soler, M.A.; Sharpless, K. B. Tetrahedron, 1995, 51, 1345.
13. Taylor, E.C.; Chiang, C.-S. Synthesis, 1977, 467.
14. Sinha, S.C.; Sinha-Bagchi, A.; Keinan, E. J. Org. Chem., 1993, 58, 7789.
15. (b) Sharpless, K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.A.; Hartung, J.; Jeong, K.S.; Kwong, H.L.; Morikawa, K.; Wang, Z.M.; Xu, D.; Zhang, X.L. J. Org. Chem., 1992, 57, 2768.
16. Villieras, J.; Rambaud, M. Synthesis, 1983, 300.
17. Dale, J.A.; Dull, D.L.; Mosher, H.S. J. Org. Chem., 1969, 34, 2543.
18. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092.
19. Takacs, J.M.; Helle, M.A.; Seely, F.L. Tetrahedron Lett., 1986, 27, 1257.
20. Authors are grateful to Prof. K.B. Sharpless for some useful suggestions received during the course of the work.
21. Still, W.C.; Kahn, M.; Mirta, A. J. Org. Chem., 1978, 43, 2923.