Total Synthesis of Antiausterity Agent (±)-Uvaridacol L by Regioselective Axial Diacylation of a myo-Inositol Orthoester.

The antiausterity natural product (±)-uvaridacol L was synthesized for the first time in seven steps from myo-inositol. The key reaction of this synthesis, axial selective dibenzoylation of myo-inositol orthoformate, was achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF). The preferential cytotoxicity of racemic uvaridacol L against cancer cell lines able to adapt to nutrient deprivation was also evaluated under nutrient deprived conditions. Morphological evaluation was also carried out.