Efficient syntheses of six potentially useful optically pure macroheterocycles with ester and dihydrazide fragments were developed from available natural Δ3-carene through intermediate (31R,33S)-32,32-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid using in the key steps [2+1]-reactions of the last with di- or triethylene glycol and [1+1]-condensation of the resulting α,ω-diketodiesters with several dicarboxylic acid dihydrazides. The structures of the obtained compounds were confirmed by IR and NMR spectroscopy and LC-MS.
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L. A. Kheifits and V. M. Dashunin, Fragrances and Other Products for Perfumery [in Russian], Khimiya, Moscow, 1994, 256 pp.
G. Yu. Ishmuratov, Yu. V. Legostaeva, L. R. Garifullina, L. P. Botsman, R. R. Muslukhov, and G. A. Tolstikov, Russ. J. Org. Chem., 50, 1075 (2014).
G. Yu. Ishmuratov, Yu. V. Legostaeva, L. R. Garifullina, L. P. Botsman, R. R. Muslukhov, N. M. Ishmuratova, and G. A. Tolstikov, Russ. J. Org. Chem., 50, 928 (2014).
K. Gajcy, J. Pekala, B. Frackowiak-Wojtasek, T. Librowski, and S. Lochynski, Tetrahedron: Asymmetry, 21, 2015 (2010).
G. A. Tolstikov, F. Z. Galin, V. K. Ignatyuk, Yu. A. Kashina, and L. M. Zelenova, Chem. Nat. Compd., 28, 295 (1992).
L. L. Frolova, A. V. Popov, L. V. Bezuglaya, I. N. Alekseev, P. A. Slepukhin, and A. V. Kuchin, Russ. J. Gen. Chem., 83, 1541 (2013).
P. A. Krasutskii, A. A. Fokin, A. V. Gulevich, A. G. Yurchenko, and V. K. Promonenkov, Zh. Org. Khim.,28, 1098 (1992).
M. H. Bolli, C. Muller, B. Mathys, S. Abele, M. Birker, R. Bravo, D. Bur, P. Hess, C. Kohl, D. Lehmann, O. Nayler, M. Rey, S. Meyer, M. Scherz, G. Schmidt, B. Steiner, A. Treiber, J. Velker, and T. Weller, J. Med. Chem., 56, 9737 (2013).
L. G. Nair, A. Saksena, R. Lovey, M. Sannigrahi, J. Wong, J. Kong, X. Fu, and V. Girijavallabha, J. Org. Chem., 75, 1285 (2010).
A. K. Saksena, V. M. Girijavallabhan, R. G. Lovey, E. Jao, F. Bennett, J. L. McCormick, H. Wang, R. E. Pike, S. L. Bogen, T.-Y. Chan, et al., U.S. Pat. Appl. 20070032433, Feb. 8, 2007.
F. Z. Macaev and A. V. Malkov, Tetrahedron, 62, 9 (2006).
Yu. A. Zolotov, A. A. Formanovskii, I. V. Pletnev, M. K. Beklemishev, S. G. Dmitrienko, N. V. Isakova, N. A. Pasekova, and E. I. Morosanova, Macrocyclic Compounds in Analytical Chemistry [in Russian], Nauka, Moscow, 1993, 320 pp.
M. Hiraoka, Studies in Organic Chemistry, Vol. 12: Crown Compounds. Their Characteristics and Applications, Elsevier, Amsterdam, Oxford, New York, 1982.
E. V. Boltukhina, A. E. Sheshenev, and I. M. Lyapkalo, Tetrahedron, 67, 5382 (2011).
K. Weygand and G. Hilgetag, Organisch-chemische Experimentierkunst, Barth, Leipzig, 1964.
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The work was performed on State Task Topic No. AAAA-A17-117011910023-2.
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2020, pp. 419–423.
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Yakovleva, M.P., Denisova, K.S., Mingaleeva, G.R. et al. Synthesis from Δ3-Carene of Optically Active Macrolides with Fragments of Di- and Triethyleneglycol and Hydrazides of Dicarboxylic Acids. Chem Nat Compd 56, 487–491 (2020). https://doi.org/10.1007/s10600-020-03068-1
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DOI: https://doi.org/10.1007/s10600-020-03068-1