Summary
Intramolecular cyclization reactions were investigated, and the configurations were proved of 2- and 3-substituted 10-oxo-9-hydroxy-9-methyl-1,2,3,4a,9,9a.10-octahydroanthracenes of type (I), which are possible intermediaries for the synthesis of tetracyclines and their analogs.
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M. M. Shemyakin, M. N. Kolosov, Hsieh Yü-yüan, M. G. Karapetyan, Shên Huai-yü, and A. I. Gurevich, Izv. AN SSSR. Ser. khim.1020 (1964).
M. M. Shemyakin, M. N. Kolosov, M. G. Karapetyan, and E. S. Chaman, Dokl. AN SSSR112, 669 (1957).
H. H. Inhoffen, H. Muxfeldt, H. Schaefer, and H. Krämer, Croat, Chem. Acta29, 329 (1957).
W. Hückel and E. Brinkmann, Ann.441, 21 (1925).
D. S. Noyce and D. B. Denney, J. Amer. Chem. Soc.72, 5743 (1950); W. G. Dauhen, G. F. Fonken, and D. S. Noyce, J. Amer. Chem. Soc.78, 2579 (1956).
Yu. P. Volkov, M. N. Kolosov, V. G. Korobko, and M. M. Shemyakin, Izv. AN SSSR. Ser. khim. 492 (1964).
Yu. A. Arbuzov, I. G. Bolesov, V. P. Bregadze, M. N. Kolosov, M. M. Shemyakin, and E. A. El'perina, Izv. AN SSSR. Ser. khim. 310 (1964).
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Translated from Izvestiya Akademii Nauk SSSR, Setiya Khimicheskaya, No. 6, pp. 1024–1035, June, 1964
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Shemyakin, M.M., Kolosov, M.N., Karapetyan, M.G. et al. Tetracyclines Communication 22. Stereochemistry of 2- and 3-substituted 10-oxo-9-hydroxy-9-methyl-1,2,3,4,4a,9,9a,10-octahydroanthracenes. Russ Chem Bull 13, 953–962 (1964). https://doi.org/10.1007/BF01141647
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DOI: https://doi.org/10.1007/BF01141647