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An investigation in the field of the stereochemistry of cyclic compounds

Communication 42. Synthesis and catalytic hydrogenation of 7-methoxy-1,2-bis-(hydroxymethyl)-hexahydrophenanthrenes

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Summary

  1. 1.

    The 7-methoxy-1,2-bis-(hydroxymethyl)-hydrophenanthrenes (VI), (VIII), (IX), and (X) have been synthesized by the lithium aluminium hydride reduction of the dimethyl esters of cis-cis-Δ4- and cis-Δ4a(10a)-7-methoxyhexahydrophenanthrene-1,2-dicarboxylic acids (V) and (VII) and the dimethyl esters of cis-syn-cis- and cis-anti-cis-7-methoxyoctahydrophenanthrene-1,2-dicarboxylic acids (XI) and (XIII).

  2. 2.

    The hydrogenation of the 7-methoxy-1,2-bis-(hydroxymethyl)-hexahydrophenanthrenes (VI) and (VIII) over 30%Pd/SrCO3 takes place spatially non-selectively and leads to a mixture of the two possible geometrical isomers of 7-methoxy-1,2-bis-(hydroxymethyl)-octahydrophenanthrene.

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Literature cited

  1. 1.

    V. F. Kucherov, V. M. Andreev, and I. N. Nazarov, Izv. AN SSSR. Otd. khim. n. 1244 (1959).

  2. 2.

    I. N. Nazarov, V. F. Kucherov, and V. M. Andreev, Izv. AN SSSR, Otd. khim. n. 715 (1956).

  3. 3.

    V. F. Kucherov, V. M. Andreev, and L. K.Lysanchuk, Izv. AN SSSR. Otd. khim. n. 1796 (1960); V. M. Andreev, L. K. Lysanchuk, and V. F. Kucherov, Izv. AN SSSR. Otd. khim. n. 1804 (1960).

  4. 4.

    W. S. Johnson et al., J. Amer. Soc.78, 6296 (1956).

  5. 5.

    V. F. Kucherov, L. K. Lysanchuk, and V. M. Andreev, Izv. AN SSSR, Otd. khim. n. 2003 (1960).

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Andreev, V.M., Kucherov, V.F. An investigation in the field of the stereochemistry of cyclic compounds. Russ Chem Bull 10, 1525–1528 (1961). https://doi.org/10.1007/BF00906145

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Keywords

  • Hydrogenation
  • Aluminium
  • Ester
  • Lithium
  • Dimethyl