참고문헌
- Bedel, O., Haudrechy, A., and LangloisY., A stereoselective formal synthesis of (-)-fumagillol. Eur. J. Org. Chem., 3813- 2819 (2004) https://doi.org/10.1002/ejoc.200400262
- Boiteau, J. G., Van de Weghe, P., and Eustache, J., A new, ring closing metathesis-based synthesis of (-)-fumagillol. Org. Lett., 3, 2737-2740 (2001) https://doi.org/10.1021/ol016343z
- Burke, S. D., Fobare, W. F., and Pacofsky, G. J., Chelation control of enolate geometry. Acyclic diastereoselection via the enolate Claisen rearrangement. J. Org. Chem., 48(26), 5221-5228 (1983) https://doi.org/10.1021/jo00174a013
-
Corey, E. J. and Snider, B. B. Total synthesis of (
${\pm}$ )-fumagillin. J. Am. Chem. Soc., 94(7), 2549-2550 (1972) https://doi.org/10.1021/ja00762a080 - Eustache, J. and van de Weghe, The ring-Closing metathesis approach to fumagillol, Strategies and Tactics in Organic Synthesis, Elsevier, Londen, 4, 247-267 (2004)
- Fardis, M., Pyun, H. J., Tario, J., Jin, H., Kim, C. U., Ruckman, J., Lin, Y., Greean, L, and Hicke, B., Design, synthesis and evaluation of a series of novel fumagillin analogues. Bioorg. Med. Chem., 11, 5051-5058 (2003) https://doi.org/10.1016/j.bmc.2003.08.031
- Folkman, J. and Ingber, D., Inhibition of angiogenesis. Seminars in cancer biology. 3, 89-96 (1992)
- Griffith, E. C., Su, Z., Turk, B. E., Chen, S., Charng, Y, -H., Wu, Z., Biemann, K., and Liu, J. O., Methionine aminopeptidase (type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin. Chem. Biol., 4(6), 461-471 (1997) https://doi.org/10.1016/S1074-5521(97)90198-8
- Gurjar, M. K., Patil, V. J., and Pawar, S. M. Synthesis of (1R,5R)-2,6-dioxabicyclo [3.3.0]octan-3-one from D-glucose. Carbohyd. Res., 165(2), 313-317 (1987) https://doi.org/10.1016/0008-6215(87)80108-8
- Haga, M., Takano, M., and Tejima, S., 3-O-Methyl-D-allose and a facile route to 2- and 3-O-methyl-D-riboses. Carbohyd. Res., 21(3), 440-446 (1972) https://doi.org/10.1016/S0008-6215(00)84925-3
- Han, C. K., Ahn, S. K., Choi, N. S., Hong, R. K., Moon, S. K., Chun, H. S., Lee, S. J., Kim, J. W., Hong, C. I., Kim, D., Yoon, J. H., and No, K. T., Design and synthesis of highly potent fumagillin analogues from homology modeling for a human MetAP-2. Bioorg. Med. Chem. Lett., 10(1), 39-43 (2000) https://doi.org/10.1016/S0960-894X(99)00577-6
- Hanson, T. E. and Eble F. R., An antiphage agent isolated from Aspergillus sp. J. Bact., 58, 527-529 (1949)
- Hutchings, M., Moffat, D., and Simpkins, N. S., A concise synthesis of fumagillol. Synlett., 5, 661-663. (2001)
- Ingber, D. E., Extracellular matrix as a solid-state regulator in angiogenesis: identification of new targets for anti-cancer therapy. Seminars in cancer biology., 3, 57-63 (1992)
- Ingber, D., Fujita, T., Kishimoto, S., Sudo, K., Kanamaru, T., Brem, H., and Folkman, J., Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth. Nature, 345, 555-557 (1990) https://doi.org/10.1038/348555a0
- Iversen, T. and Bundle, D. R., Benzyl trichloroacetimidate, a versatile reagent for acid-catalyzed benzylation of hydroxygroups. J. Chem. Soc., Chem. Commun., 23, 1240-1243, (1981) https://doi.org/10.1039/c39810001240
- Kallmerten, J. and Gould, T. J., Enolate Claisen rearrangement of glycolate esters. Tetrahedron Lett., 24, 5177-5180 (1983) https://doi.org/10.1016/S0040-4039(00)88390-2
- Katznelson, H. and Jamieson, C. A., Control of nosema disease of honeybees with fumagillin. Science, 115, 70-71 (1952) https://doi.org/10.1126/science.115.2977.70
- Killough, J. J., Magill, G. B., and Smith, R. C. The treatment of amebiasis with fumagillin. Science, 115, 71-72 (1952) https://doi.org/10.1126/science.115.2977.71
- Kim, D., Ahn, S. K., Bae, H., Choi, W. J., and Kim, H. S., An asymmetric total synthesis of (-)-fumagillol. Tetrahedron Lett., 38(25), 4437-4440 (1997) https://doi.org/10.1016/S0040-4039(97)00925-8
- Kim, D., Min, J., Ahn, S. K., Lee, H. W., Choi, N. S., and Moon, S. K., 5-Demethoxyfumagillol, a potent angiogenesis inhibitor isolated from Aspergillus Fumagatus. Chem. Pharm. Bull., 52, 447-450 (2003) https://doi.org/10.1248/cpb.52.447
- McCowen M. C., Callender, M. E., and Lawlis, J. F. Jr., Fumagillin (H-3), a new antibiotic with amebicidal properties. Science, 113, 202-203 (1951) https://doi.org/10.1126/science.113.2930.202
- Mitsunobu, O., The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis, 1, 1-28 (1981) https://doi.org/10.1055/s-1981-29317
- Roush, W. R., Ando, K., Powers, D. B., Halterman, R. I., and Palkowitz, A. D., Enantioselective synthesis using diisopropyl tartrate-modified (E)- and (Z)-crotylboronates: reactions with achiral aldehydes. Tetrahedron Lett., 29, 5579-5582 (1988) https://doi.org/10.1016/S0040-4039(00)80816-3
- Roush, W. R., Waltz, A. E., and Hong, L. K., Diastereo- and enantioselective aldehyde addition reactions of 2-allyl-1,3,2- dioxaborolane-4,5-dicarboxylic esters, a useful class of tartrate ester modified allylboronates. J. Am. Chem. Soc., 107, 8186 -8190 (1985) https://doi.org/10.1021/ja00312a062
- Sato, T., Tajima, K., and Fujisawa, T., Diastereoselective synthesis of erythro- and threo-2-hydroxy-3-methyl-4- pentenoic acids by the ester enolate Claisen rearrangement of 2-butenyl 2-hydroxyacetate. Tetrahedron Lett., 24(7), 729- 730 (1983) https://doi.org/10.1016/S0040-4039(00)81510-5
- Sin, N., Meng, L., Wang, M. Q. W., Wen, J. J., Bornmann, W.G., and Crews, C. M., The anti-angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2. Proc. Natl. Acad. Sci. USA, 94, 6099-6103 (1997) https://doi.org/10.1073/pnas.94.12.6099
- Steglich, W. and Neises, B., 4-Dialkylaminopyridines as acylation catalysts. 5. Simple method for the esterification of carboxylic acids. Angew. Chem., 90, 556-557 (1978) https://doi.org/10.1002/ange.19780900718
- Taber, D. F., Christos, T. E., Rheingold, A. L., and Guzei, I. A., Synthesis of (-)-Fumagillin. J. Am. Chem. Soc., 121, 5589- 5590 (1999) https://doi.org/10.1021/ja990784k
- Tarbell, D. S., Carman R. M., Chapman, D. D., Cremer, S. E., Cross, A. D., Huffman, K. R., Kunstmann, M., McCorkindale, N. J., McNally, J. G. Jr., Rosowsky, A., Varino, F. H. L., and West, R. L. The chemistry of fumagillin. J. Am. Chem. Soc., 83, 3096-3113 (1961) https://doi.org/10.1021/ja01475a029
- Tarbell, D. S., Carman, R. M., Chapman, D. D., Huffman, K. R., and McCorkindale, N. J., Structure of fumagillin. J. Am. Chem. Soc., 82, 1005-1007 (1960) https://doi.org/10.1021/ja01489a067
- Vosburg, D. A., Weiler, S., and Sorensen, E. J., A concise synthesis of fumagillol. Angew. Chem. Int. Ed., 38, 971-974 (1999) https://doi.org/10.1002/(SICI)1521-3773(19990401)38:7<971::AID-ANIE971>3.0.CO;2-W
- Vosburg, D. A., Weiler, S., and Sorensen, E. J., Concise stereocontrolled routes to fumagillol, fumagillin, and TNP- 470. Chirality, 15, 156-166 (2003) https://doi.org/10.1002/chir.10181
- Zhang, P., Nicholson, D. E., Bujnicke, J. M., Su, X., Brendle, J. J., Ferdig, M., Kyle, D. E., Milhous, W. K., and Chiang, P. K., Angiogenesis inhibitors specific for methionine aminopeptidase 2 as drugs for malaria and leishmaniasis. J. Biomed. Sci., 9, 34-40 (2002) https://doi.org/10.1007/BF02256576