Enantioselective synthesis of natural combretastatin

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1101-1104

  Ramacciotti, Alessio ^a   Fiaschi, Rita ^a   Napolitano, Elio ^a,b  

^a UNIVERSITY OF PISA   (Italy)

^b SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COMBRETASTATIN;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029872939     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00115-2     Document Type: Article

References (12)

1. Studies of structure-activity relationship with combretastatine analogues: (a) Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. J. Med. Chem. 1995, 38, 1666, and references cited therein.
2. (b) Medarde, M.; Pelaez-Lamamié de Clairac, R.; Ramos, A. C.; Caballero, E.; Lopez, J. L.; Gravalos, D. G.; San Feliciano, A. Bioorg. Med. Chem. Lett. 1995, 5, 229.
3. (c) Nandy, P.; Banerjee, S.; Gao, H.; Hui, M. B. V.; Lien, E. J. Pharm. Res. 1991, 8, 776.
4. Other syntheses of racemic combretastatin: (d) Mannila, E.; Talvitie, A. Liebig Ann. Chem. 1993, 1037.
5. (e) Napolitano, E.; Fiaschi, R.; Marsili, A. Gazz. Chim. Ital. 1988, 118, 415.
6. Pettit, G. R.; Singh, S. B.; Cragg, G. M. J. Org. Chem. 1985, 50, 3404.
7. Kolb, H. C.; VanNieuwenhze M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
8. Cristol, S. J.; Douglass, J. R.; Meek, J. S. J. Am. Chem. Soc. 1951, 73, 816.
9. Hindmarsh, E. M.; Knight, I.; Robinson, R. J. Chem. Soc. 1917, 940.
10. Gorzinski Smith J. Synthesis 1984, 629. A further application of this reaction to the enantioselective synthesis of (+)-phillodulcin (a natural isocoumarin) will appear in the due course.
11. Pettit, G. R.; Cragg, G. M.; Singh, S. B. J. Nat. Prod. 1987, 50, 386.
12. Still, W. C.; Kahn, M.; Mitra, A. P. J. Org. Chem. 1978, 43. 2923.