Abstract
3-Methoxy-4-hydroxy-5-methyl-2-cyclopentenone (VI), a good model for five-membered vinylogous ester of acutumine (I), was reduced with lithium aluminum hydride, to 4-methyl-5-hydroxy-2-cyclopentenone (X), 2-methyl-4-cyclopentene-1, 3-diol (XI(VI)) and 2-methyl-cyclopentane-1, 3-diol (XII(VI)). 3-Methoxy-4-methyl-5-hydroxy-2-cyclopentenone (VII) was reduced to 4-hydroxy-5-methyl-2-cyclopentenone (XIII). The revised mechanism was proposed and the errors in the previous papers based on ambiguous experimental data were corrected.
