Stereoselective heck-matsuda arylations of chiral dihydrofurans with arenediazonium tetrafluoroborates; an efficient enantioselective total synthesis of (-)-isoaltholactone

The Heck-Matsuda arylation of chiral 2-( S)-hydroxy-methyl dihydrofurans (endocyclic enolethers) and its derivatives, employing arenediazonium tetrafluoroborates, was developed into a highly efficient, practical and diastereoselective synthetic process. This methodology was applied to the total synthesis of the styryllactone (-)-isoaltholactone in seven steps with an overall yield of ~25%, from the readily available chiral 2-hydroxymethyldihydrofuran. The strategy permits the synthesis of several other aromatic analogues of isoaltholactone.