Enantiospecific synthesis of (-)-trachyspic acid

Abstract

The enantiospecific synthesis of (-)-trachyspic acid is presented. The D-oxyribose derived alcohol was oxidized in one step to the acid and esterification with allyl alcohol provided ester. Alkylation of the anion derived from dimethyl malonate with nonyl bromide produced diester which was reduced to diol in excellent yield. An enantiospecific synthesis of the unnatural enantiomer of trachyspic acid was achieved, confirming the absolute configuration of this compound.