Abstract
The Heck-Matsuda arylation of chiral 2-(S )-hydroxymethyl 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.
Key words
Heck reaction - palladium - diazonium compounds - catalysis - stereoselectivity
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