Keywords: Natural products / Total synthesis / Homogeneous catalysis / PalladiumThe total synthesis of natural (+)-varitriol (1) was accomplished by starting from dimethyl L-tartrate. The key features were a substrate selective and diastereoselective Pd II -catalysed bicyclisation of unsaturated protected triol 9 followed by regioselective ring-opening of bicyclic skeleton
A short and efficient total synthesis of cytotoxic natural (+)-varitriol has been accomplished in eight steps from g-D-ribonolactone and 2,3-dimethylanisole in 41% overall yield. The key features include a highly stereoselective introduction of methyl at a carbonyl group and installation of the side chain with the aromatic portion by Julia-Kocieński olefination at C5 of the starting carbon skeleton.
SummaryThe study of Pd-catalysed cyclisation reactions of alkenols using different catalytic systems is reported. These transformations affect the stereoselective construction of mono- and/or bicyclic oxaheterocyclic derivatives depending on a starting alkenol. The substrate scope and proposed mechanism of Pd-catalysed cyclisation reactions are also discussed. Moreover, the diastereoselective Pd-catalysed cyclisation of appropriate alkenols to tetrahydrofurans and subsequent cyclisation provided properly substituted 2,5-dioxabicyclo[2.2.1]heptane and 2,6-dioxabicyclo[3.2.1]octane, respectively. Such bicyclic ring subunits are found in many natural products including ocellenynes and aurovertines.
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