Stereochemistry of cyclic compounds Communication 17. Condensation of 1-(1-acetoxyvinyl) cyclohexene with maleic anhydride

1. The condensation of 1-(1-ace toxyvinyl)cyclohexene (I) with maleic anhydride was studied: it results in an 80% yield of the anti-cis anhydride (III), which is quantitatively hydrolyzed by water to anti-cis-4-acetoxy 1,2,3,5,6,7,8,8a-octahydro-1,2-naphthalenedicarboxylic acid (IV), which gives the anti-cis acetoxy diester (V) with diazomethane. 2. By hydrolysis of the acetoxy group in the acid (IV) and the diester (V) we prepared the traps-anti-cis keto acid (VI) and the traps-anti-traps keto diester (X), and Clemmensen reduction of these gave the previously described traps-anti-cis decahydro-1,2-naphthalenedicarboxylic acid (IX) and the traps-anti-traps-decahydro 1,2-naphthalenedicarboxylic diester (XI), thus confirming the configurations of these last compounds. 3. The steric transformations of some monoesters of this series were studied, and it was shown that they readily undergo isomerization at the 2-alkoxycarbonyl group.