Concise Enantio- and Diastereoselective Total Syntheses of Fumagillol, RK-805, FR65814, Ovalicin, and 5-Demethylovalicin†
Junichiro Yamaguchi
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMaya Toyoshima
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMitsuru Shoji Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorHideaki Kakeya Dr.
Antibiotics Laboratory, Discovery Research Institute, RIKEN, Wako, Saitama 351-0198, Japan
Search for more papers by this authorHiroyuki Osada Prof. Dr.
Antibiotics Laboratory, Discovery Research Institute, RIKEN, Wako, Saitama 351-0198, Japan
Search for more papers by this authorYujiro Hayashi Prof. Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorJunichiro Yamaguchi
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMaya Toyoshima
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMitsuru Shoji Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorHideaki Kakeya Dr.
Antibiotics Laboratory, Discovery Research Institute, RIKEN, Wako, Saitama 351-0198, Japan
Search for more papers by this authorHiroyuki Osada Prof. Dr.
Antibiotics Laboratory, Discovery Research Institute, RIKEN, Wako, Saitama 351-0198, Japan
Search for more papers by this authorYujiro Hayashi Prof. Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorThis paper is dedicated to Prof. E. J. Corey for his elegant total syntheses of the fumagillin and ovalicin families. This work was partially supported by a Grant-in-Aid for Scientific Research on Priority Areas 16073219 from The Ministry of Education, Culture, Sports, Science, and Technology (MEXT).
Graphical Abstract
L-Proline-mediated α-aminoxylation is a key step in the enantio- and diastereoselective total syntheses of fumagillin, ovalicin, and related compounds (see scheme). These compounds contain a cyclohexane ring, two epoxides, and five or six contiguous stereogenic centers, and they display anti-angiogenesis or immunosuppressive properties.
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