28976-76-3Relevant academic research and scientific papers
Total synthesis of (+)-jatrophone
Han, Qi,Wiemer, David F.
, p. 7692 - 7697 (2007/10/02)
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-Horner-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.
