TOTAL SYNTHESIS OF (+)-JATROPHONE

The first total synthesis of optically active (+)-jatrophone is described. A convergent sequence provides the natural enantiomer in just 12 steps from (R)-(+)-3-methyladipic acid. Key steps include formation of the jatrophone C-ring through a Wadsworth-Homer-Emmons variant, a Pd-catalyzed cross-coupling that incorporates the C5-C6 double bond with the required Z-stereochemistry, and formation of the macrocycle by condensation of an acetylenic aldehyde. This sequence provides a short, efficient, and stereocontrolled route to the complex diterpenoid (+)-jatrophone.