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).
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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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