Synfacts 2006(8): 0749-0749  
DOI: 10.1055/s-2006-941931
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Fumagillol, RK-805, and FR65814

Contributor(s): Philip Kocienski, Thomas Snaddon
J. Yamaguchi, M. Toyoshima, M. Shoji, H. Kakeya, H. Osada, Y. Hayashi*
Tokyo University of Science and Riken, Saitama, Japan
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Publikationsverlauf

Publikationsdatum:
21. Juli 2006 (online)

Significance

The target molecules are angiogenesis inhibitors except FR65814, which is an immunosuppressant. Noteworthy features of this synthesis include (1) the l-proline-catalyzed enantioselective α-aminoxylation reaction (see Y. Hayashi et al. Angew. Chem. Int. Ed. 2004, 43, 1112-1115 and Tetrahedron Lett. 2003, 44, 8293-8296), and (2) the hydroxyl-directed conjugate addition of an organozinc species. The syntheses of Ovalicin and 5-Demethylovalicin are also described.