Synthesis of (-)-Fumagillin

Journal of the American Chemical Society

Volumn 121, Issue 23, 1999, Pages 5589-5590

  Taber, Douglass F ^a   Christos, Thomas E ^a   Rheingold, Arnold L ^a   Guzei, Ilia A ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; ANTINEOPLASTIC AGENT; FUMAGILLIN; KETONE;

ANGIOGENESIS; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0033575093     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990784k     Document Type: Article

References (33)

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9. For leading references both to the isolation of fumagillin and to the use of semisynthetic derivatives as antiangiogenic agents, see the following: (a) Hanson, T. E. Antibiot. Chemother. (Washington, D.C.) 1951, 1, 54. (b) Marui, S.; Itoh, Y.; Kosai, Y.; Sudo, K.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 96. (c) Marui, S.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 575. (d) Marui, S.; Yamamoto, T.; Sudo, K.; Akimoto, H.; Kishimoto, S. Chem. Pharm. Bull. 1995, 43, 588. (e) Dorey, G.; Leon, P.; Sciberras, S.; Leonce, S.; Guilbaud, N.; Pierre, A.; Atassi, G.; Billington, D. C. Bioorg. Med. Chem. Lett. 1996, 6, 3045. (e) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang, Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183.
10. For leading references both to the isolation of fumagillin and to the use of semisynthetic derivatives as antiangiogenic agents, see the following: (a) Hanson, T. E. Antibiot. Chemother. (Washington, D.C.) 1951, 1, 54. (b) Marui, S.; Itoh, Y.; Kosai, Y.; Sudo, K.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 96. (c) Marui, S.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 575. (d) Marui, S.; Yamamoto, T.; Sudo, K.; Akimoto, H.; Kishimoto, S. Chem. Pharm. Bull. 1995, 43, 588. (e) Dorey, G.; Leon, P.; Sciberras, S.; Leonce, S.; Guilbaud, N.; Pierre, A.; Atassi, G.; Billington, D. C. Bioorg. Med. Chem. Lett. 1996, 6, 3045. (e) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang, Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183.
11. For leading references both to the isolation of fumagillin and to the use of semisynthetic derivatives as antiangiogenic agents, see the following: (a) Hanson, T. E. Antibiot. Chemother. (Washington, D.C.) 1951, 1, 54. (b) Marui, S.; Itoh, Y.; Kosai, Y.; Sudo, K.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 96. (c) Marui, S.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 575. (d) Marui, S.; Yamamoto, T.; Sudo, K.; Akimoto, H.; Kishimoto, S. Chem. Pharm. Bull. 1995, 43, 588. (e) Dorey, G.; Leon, P.; Sciberras, S.; Leonce, S.; Guilbaud, N.; Pierre, A.; Atassi, G.; Billington, D. C. Bioorg. Med. Chem. Lett. 1996, 6, 3045. (e) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang, Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183.
12. For leading references both to the isolation of fumagillin and to the use of semisynthetic derivatives as antiangiogenic agents, see the following: (a) Hanson, T. E. Antibiot. Chemother. (Washington, D.C.) 1951, 1, 54. (b) Marui, S.; Itoh, Y.; Kosai, Y.; Sudo, K.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 96. (c) Marui, S.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 575. (d) Marui, S.; Yamamoto, T.; Sudo, K.; Akimoto, H.; Kishimoto, S. Chem. Pharm. Bull. 1995, 43, 588. (e) Dorey, G.; Leon, P.; Sciberras, S.; Leonce, S.; Guilbaud, N.; Pierre, A.; Atassi, G.; Billington, D. C. Bioorg. Med. Chem. Lett. 1996, 6, 3045. (e) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang, Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183.
13. For leading references both to the isolation of fumagillin and to the use of semisynthetic derivatives as antiangiogenic agents, see the following: (a) Hanson, T. E. Antibiot. Chemother. (Washington, D.C.) 1951, 1, 54. (b) Marui, S.; Itoh, Y.; Kosai, Y.; Sudo, K.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 96. (c) Marui, S.; Kishimoto, S. Chem. Pharm. Bull. 1992, 40, 575. (d) Marui, S.; Yamamoto, T.; Sudo, K.; Akimoto, H.; Kishimoto, S. Chem. Pharm. Bull. 1995, 43, 588. (e) Dorey, G.; Leon, P.; Sciberras, S.; Leonce, S.; Guilbaud, N.; Pierre, A.; Atassi, G.; Billington, D. C. Bioorg. Med. Chem. Lett. 1996, 6, 3045. (e) Griffith, E. C.; Su, Z.; Niwayama, S.; Ramsay, C. A.; Chang, Y.-H.; Liu, J. O. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15183.
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15. For synthetic approaches to fumagillin, see the following: (a) Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549. (b) Kim, D.; Ahn, S. K.; Bae, H.; Choi, W. J.; Kim, H. S. Tetrahedron Lett. 1997, 38, 4437.
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17. For syntheses of ovalicin, see the following: (a) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256. (b) Bath, S.; Billington, D. C.; Gero, S. D.; Quiclet-Sire, B.; Samadi, M. J. Chem. Soc., Chem. Commun. 1994, 1495. (c) Corey, E. J.; Guzman-Perez, A.; Noe, M. J Am. Chem. Soc. 1994, 116, 12109. (d) For a synthesis of FR65814, see the following: Amano, S.; Ogawa, N.; Ohtsuka, M.; Chida, N. Tetrahedron 1999, 55, 2205.
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19. For syntheses of ovalicin, see the following: (a) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256. (b) Bath, S.; Billington, D. C.; Gero, S. D.; Quiclet-Sire, B.; Samadi, M. J. Chem. Soc., Chem. Commun. 1994, 1495. (c) Corey, E. J.; Guzman-Perez, A.; Noe, M. J Am. Chem. Soc. 1994, 116, 12109. (d) For a synthesis of FR65814, see the following: Amano, S.; Ogawa, N.; Ohtsuka, M.; Chida, N. Tetrahedron 1999, 55, 2205.
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