A Stereoselective Asymmetric Synthesis of Antibiotic (-)-Fumagillol Using Claisen Rearrangement and Intramolecular Ester Enolate Alkylation as Key Steps |
Kim Deukjoon
(College of Pharmacy, Seoul National University)
Ahn Soon Kil (New Drug Research Laboratories, Chong Kun Dang Research Institute Cheonan) Bae Hoon (Department of Chemistry and Biochemistry, Florida State University) Kim Hak Sung (Wonkwang University, College of Pharmacy) |
1 | Hutchings, M., Moffat, D., and Simpkins, N. S., A concise synthesis of fumagillol. Synlett., 5, 661-663. (2001) |
2 | 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) DOI |
3 | Killough, J. J., Magill, G. B., and Smith, R. C. The treatment of amebiasis with fumagillin. Science, 115, 71-72 (1952) DOI PUBMED |
4 | 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) DOI ScienceOn |
5 | 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) DOI PUBMED |
6 | Mitsunobu, O., The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis, 1, 1-28 (1981) DOI |
7 | Taber, D. F., Christos, T. E., Rheingold, A. L., and Guzei, I. A., Synthesis of (-)-Fumagillin. J. Am. Chem. Soc., 121, 5589- 5590 (1999) DOI ScienceOn |
8 | 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) DOI |
9 | 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) DOI ScienceOn |
10 | Hanson, T. E. and Eble F. R., An antiphage agent isolated from Aspergillus sp. J. Bact., 58, 527-529 (1949) |
11 | 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) DOI |
12 | Kallmerten, J. and Gould, T. J., Enolate Claisen rearrangement of glycolate esters. Tetrahedron Lett., 24, 5177-5180 (1983) DOI ScienceOn |
13 | 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) |
14 | Bedel, O., Haudrechy, A., and LangloisY., A stereoselective formal synthesis of (-)-fumagillol. Eur. J. Org. Chem., 3813- 2819 (2004) DOI ScienceOn |
15 | Corey, E. J. and Snider, B. B. Total synthesis of ()-fumagillin. J. Am. Chem. Soc., 94(7), 2549-2550 (1972) DOI PUBMED |
16 | 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) DOI ScienceOn |
17 | 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) DOI |
18 | 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) DOI ScienceOn |
19 | Katznelson, H. and Jamieson, C. A., Control of nosema disease of honeybees with fumagillin. Science, 115, 70-71 (1952) DOI PUBMED |
20 | 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) DOI ScienceOn |
21 | 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) DOI ScienceOn |
22 | 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) |
23 | Vosburg, D. A., Weiler, S., and Sorensen, E. J., A concise synthesis of fumagillol. Angew. Chem. Int. Ed., 38, 971-974 (1999) DOI |
24 | Vosburg, D. A., Weiler, S., and Sorensen, E. J., Concise stereocontrolled routes to fumagillol, fumagillin, and TNP- 470. Chirality, 15, 156-166 (2003) DOI ScienceOn |
25 | Folkman, J. and Ingber, D., Inhibition of angiogenesis. Seminars in cancer biology. 3, 89-96 (1992) |
26 | 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) DOI ScienceOn |
27 | 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) DOI ScienceOn |
28 | 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) DOI ScienceOn |
29 | 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) DOI ScienceOn |
30 | 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) DOI ScienceOn |
31 | 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) DOI |
32 | 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) DOI |
33 | 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) DOI ScienceOn |
34 | 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) DOI |