Abstract: 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 CSX 6 double bond with the required 2-stereochemistry, and formation of the macrocycle by condensation of an ...
