The cytotoxic marine metabolite harzialactone A has been synthesized
stereoselectively starting from phenylacetaldehyde through three
different routes. The key steps were: in the first approach Sharpless
asymmetric dihydroxylation, in the second approach diastereoselective
iodo carbonate preparation, and in the third approach Jacobsen’s
hydrolytic kinetic resolution. In all these three schemes the triol
was successfully converted into the lactone by using highly chemoselective
oxidation with TEMPO and (diacetoxyiodo)benzene.
harzialactone A - stereoselective synthesis - Maruoka allylation - Sharpless asymmetric dihydroxylation - stereoselective iodo
carbonate preparation - Jacobsen’s hydrolytic kinetic
resolution
