Ring differentiation of the trans-decahydronaphthalene system via chemo-enzymatic dissymmetrization of its σ-symmetric glycol: Synthesis of a highly functionalized chiral building block for the terpene synthesis

The asymmetric ring differentiation by lipase-catalyzed transesterification of a meso decahydronaphthalenediol (1) was accomplished in extremely high optical and chemical yield. The absolute stereochemistry of the corresponding mono-acetate (-)-2 was determined by its conversion into a decalone [(-)-3] and to an octalone [(+)-4], which were key intermediates for the synthesis of (⊃-polygodial, (-) -warburganal, and (-)-drimenin.