Synthesis of diterpenoid acids. Part IX. Preparation of a 5-hydroxy-8-oxodecahydronaphthoic acid lactone

Abstract

The preparation of trans-decahydro-8β-hydroxy-5-oxonaphthalene-1β-carboxylic acid lactone from cis-hexahydro-5α-hydroxy-8-oxonaphthalene-1α-carboxylic acid is described. The stereochemistry of the keto-lactone was established. The results show that the stereochemistry of reduction of the ketone at the 8-position of a decahydronaphthalene-1-carboxylic acid is not affected by an axial 5-hydroxy-group.