Abstract
The 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.
Highlights
Oxaheterocycles of various sizes are found in many different biologically active compounds
Substituted tetrahydrofuran units are present in a large branch of natural products that display interesting biological properties, such as goniofufurone 1 [1], goniothalesdiol 2 [2], varitriol 3 [3], erythroskyrine 4 [4,5], ocellenynes 5 [6,7], sorangicin A 6 [8], aurovertins 7 [9,10,11,12] and epicitreoviridinol 8 [13] (Figure 1)
While the cyclisation reactions of alkenols have been relatively well described in the literature, only less attention was given to the reactions of unsaturated polyols
Summary
Oxaheterocycles of various sizes are found in many different biologically active compounds. The metal-catalysed carboetherification reactions [16,17,18] and intramolecular oxycarbonylations of alkenes [19,20,21] are of particular importance. Many of these synthetic routes have showed their potential, there is still an area for improving the scope and stereocontrol of the new synthetic construction of substituted tetrahydrofurans.
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