Abstract
1. Oxidation of the anhydride of 1, 2, 3, 5, 6, 7, 8, 8a-octahydro-1,2-naphthalenedicarboxyltc acid (III) with peroxyacetic acid gave the syn-cis 4-hydroxy y-lactone acid (V), formed by intramolecular lactonization of the epoxide (IV), which is formed intermediately. 2. Chromium trioxide oxidation of the syn-cis 4-hydroxy y-lactone acid (V) gave the syn-cis 4-oxo γ-lactone acid (VIII), and this product and its ester (IX) were used in the synthesis of trans -syn-cis-decahydro1, 2-naphthalenedicarboxylic acid (1), The latter was obtained in good yield by the hydrogenolysis of the 4=oxo γ-lactone acid (VIII), brought about by treatment at the boil with zinc in a mixture of hydrochloric acid and methanol. 3. The trans-syn-cis acid (I) that we have now synthesized is the seventh of the eight possible isomers of decahydro-1,2-naphthalenedicarboxyUc acid to be discovered. Its steric transformations were studied with the aid of molecular models. The question of the configuration and stability of the last (eighth) trans-syn-trans isomer (II) was discussed; it is very unlikely to exist under ordinary conditions.
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