Summary
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1.
The unsaturated bicyclic ketone (VIII) was obtained in 7% yield from the reaction of 2-bromomagnesium-6-methoxynaphthalene (I) with the methyl ether of dihydroresorcinol, and on being demethylated gave the model analog of homoequilenine (VII).
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2.
The reaction of p-anisylmagnesium bromide (X) with the methyl ether of dihydroresorcinol (II) led to the formation of 2-(p-methoxyphenyl)-Δ1-cyclohexen-6-one (XII) in 40% yield.
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3.
6-(p-Hydroxy-o-methylphenyl)-1-tetrahydronaphthalone (XIX) was prepared by demethylation of 6-(p-methoxy-o-methylphenyl)-1-tetrahydronaphthalone (XX) with aluminum chloride in boiling xylene.
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4.
6-(p-Hydroxyphenyl)-1-tetrahydronaphthalone (XXI) was converted into 6-(p-acetoxyphenyl)-1-tetrahydronaphthalone (XXIII) by boiling with acetic anhydride.
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5.
The tricyclic ketones (XXVII) and (XVIII) were isolated respectively by the action of the potassium derivative of 5-methoxy-2-tetrahydronaphmalone (XXVI) on 2-phenyl-1-bromoethane (XXIV) and 2-(m-methoxyphenyl)-1-bromoethane (XXV), and these after the cyclization with polyphosphoric acid and the subsequent dehydrogenation with palladium on carbon gave 1-methoxychrysene (XXXI) and 1,8-dimethoxychrysene (XXXII).
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I. N. Nazarov and S. I. Zav'ialov, Bull. Acad. Sci. USSR, Div. Chem. 1956, 569.
I. N. Nazarov and S. I. Zav'ialov, Bull. Acad. Sci. USSR, Div. Chem. 1956, 1452.
I. N. Nazarov and S. I. Zav'ialov, Bull. Acad. Sci. USSR, Div. Chem. 1957, 207.
F. C. Novello and M. E. Christy, J. Amer. Chem. Soc. 75, 5431 (1953).
F. C. Novello, M. E. Christy and J. M. Sprague, J. Amer. Chem. Soc. 75, 1330 (1953).
J. W. Cornforth and R. Robinson, J. Chem. Soc. 1949, 1861.
J. F. Collins and H. Smith, J. Chem. Soc. 1956, 4309.
K. Freis and K. Schimmel-Smidt, Ber. 58, 2835 (1925).
M. Bornstein, R. Pappo and J. Szmuszkovicz, Bull. Research Council Israel, 2, 273–275 (1952).
I. N. Nazarov and S. I. Zav'ialov, J. Gen. Chem. USSR, 23, 1703 (1953).
J. F. Norris, M. Watt and R. Thomas, J. Amer. Chem. Soc. 38, 1078 (1916).
W. E. Bachmann and D. G. Thomas, J. Amer. Chem. Soc. 64, 95 (1942).
I. W. Cook and R. Schoental, J. Chem. Soc. 1945, 291.
W. S. Johnson, et. al., J. Amer. Chem. Soc. 74, 2832 (1952).
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In conclusion, we express our gratitude to I. A. Eskin for running the tests of the estrogenic activity of the compounds described in this paper.
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Nazarov, I.N., Zav'ialov, S.I. Synthesis of steroidal compounds and substances related to them 40. Synthesis of steroid analogs which do not contain ring b or c. Russ Chem Bull 7, 1190–1195 (1958). https://doi.org/10.1007/BF00914949
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DOI: https://doi.org/10.1007/BF00914949