Summary
Various 10-oxo-9-hydroxy-9-methy 1-1,2,3,4,4a,9,9a,10-octahydroanthracenes were synthesized; they are analogous in structure to the DCB ring system of tetracyclines and have active functional groups in the 2- and 3-positions (halogen atoms, the epoxy group, hydroxyl, and ketonic carbonyl), which creates the potentiality of the further introduction of suitable substituents and then the building up of the fourth ring of tetracyclines.
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Yu. P. Volkov, M. N. Kolosov, V. G. Korobko, and M. M. Shemyakin, Izv. AN SSSR, Ser. khim.1964, 492.
M. M. Shemyakin, M. N. Kolosov, Yu. A. Arbuzov, M. G. Karapetyan, E. S. Chaman, and A. A. Onishchenko, Zh. obshch. khimii,29, 1831 (1959).
M. M. Shemyakin, M. N. Kolosov, Yu. A. Arbuzov, V. V. Onoprienko, and Hsieh Yü-yüan, Zh. obshch. khimii,30, 545 (1960).
M. M. Shemyakin, M. N. Kolosov, M. G. Karapetyan, Hsieh Yü-yüan, and V. V. Onoprienko, Izv. AN SSSR, Ser. khim. 1031 (1964).
S. Wolfe, M. Nussim, Y. Mazur, and F. Sondheimer, J. Organ. Chem.24, 1034 (1959).
E. B. Barnett and N. F. Goodway, J. Chem. Soc.1929, 1754.
M. S. Newman and H. V. Zahm, J. Amer. Chem. Sic.65, 1097 (1943).
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For communication 20 see [1].
The authors are deeply indebted to L. B. Senyavina for the measurement of infrared spectra.
Translated from Izvestiya Akademii Nauk SSSR, Setiya Khimicheskaya, No. 6, pp. 1013–1024, June, 1964
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Shemyakin, M.M., Kolosov, M.N., Yü-yüan, H. et al. Tetracyclines Communication 21. Synthesis of 2- and 3-substituted 10-oxo-9-hydroxy-9-methyl-1,2,3,4,4a,9,9a,10-octahydroanthracenes. Russ Chem Bull 13, 944–952 (1964). https://doi.org/10.1007/BF01141646
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DOI: https://doi.org/10.1007/BF01141646