The tetraacetate of glycosylated convolutamydine A was synthesized for the first time from D-glucose with subsequent construction of 3,5-dibromophenylglucopyranosylamines, tetraacetoxyglucopyranosyl-4,6-dibromoindole-2,3-diones, and cross-aldol condensation of the last with acetone. The structures of the products were elucidated using NMR and IR spectroscopy.
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W. Shi and T. L. Lowary, Bioorg. Med. Chem., 19, 1779 (2011).
G. M. Cragg, D. G. I. Kingston, and D. J. Newman, Anticancer Agents from Natural Products, CRC Press, Taylor and Francis Group, 2011, 740 pp.
Z. Xiao, Y. Hao, B. Liu, and L. Qian, Leuk. Lymphoma, 43, 1763 (2002).
M. Sassatelli, E. Saab, F. Anizon, M. Prudhomme, and P. Moreau, Tetrahedron Lett., 45, 4827 (2004).
D. Kleeblatt, C. A. Cordes, P. Lebrenz, M. Hein, H. Feist, A. Matin, R. Raza, J. Iqbal, O. Munshi, Q. Rahman, A. Villinger, and P. Langer, RSC Adv., 4, 22828 (2014).
K. M. Driller, S. Libnow, M. Hein, M. Harms, K. Wende, M. Lalk, D. Michalik, H. Reinke, and P. Langer, Org. Biomol. Chem., 6, 4218 (2008).
A. V. Stachulski and X. Meng, Nat. Prod. Rep., 30, 806 (2013).
Y. Kamano, H. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, and G. R. Pettit, Tetrahedron Lett., 36, 2783 (1995).
S. Wei, B. Schmid, F. Z. Macaev, S. N. Curlat, A. V. Malkov, and S. B. Tsogoeva, Asymmetric Catal., 1, 40 (2014).
A. V. Malkov, M. A. Kabeshov, M. Bella, O. Kysilka, D. A. Malyshev, K. Pluhackova, and P. Kocovsky, Org. Lett., 9, 5473 (2007).
G. Luppi, M. Monari, R. J. Correa, F. de A. Violante, A. C. Pinto, B. Kaptein, Q. B. Broxterman, S. J. Garden, and C. Tomasini, Tetrahedron, 62, 12017 (2006).
J. R. Chen, X. P. Liu, X. Y. Zhu, L. Li, Y. F. Qiao, W. J. Xiao, and J. M. Zhang, Tetrahedron, 63, 10437 (2007).
S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, and T. Toru, Chem. Eur. J., 14, 8079 (2008).
S. J. Gargen, J. C. Torres, A. A. Ferreira, R. B. Silva, and A. C. Pinto, Tetrahedron Lett., 38, 1501 (1997).
F. Z. Makaev, O. M. Radul, and A. P. Gudima, Russ. Chem. Bull., 7, 1571 (2008).
Acknowledgment
The work was performed under the auspices of Applied Research Project No. 15.817.02.17A.
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2016, pp. 80–83.
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Makaev, F.Z., Pogrebnoi, V.S. Synthesis of the Tetraacetate of Glycosylated Convolutamydine A. Chem Nat Compd 52, 86–89 (2016). https://doi.org/10.1007/s10600-016-1553-3
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DOI: https://doi.org/10.1007/s10600-016-1553-3