The Tsuji–Wilkinson decarbonylation proceeds under mild conditions and is highly stereospecific. In addition to aliphatic, aromatic, and α,β-unsaturated aldehydes, acyl nitriles and 1,2-diketones are also suitable substrates. Few methods exist for decarbonylation.
One illustrative application is the synthesis of the core nucleus of FR-900482. Note that the ester is unaffected by the rhodium reagent.
The Tsuji–Wilkinson decarbonylation is employed in the penultimate step of the synthesis of (–)-presilphiperfolan-8-ol. They comment “Of note in these final steps, separate reduction and oxidation steps proceeded in inferior yield in generating 38 (70% versus 93%), while the Rh(PPh)Cl operation proceeded smoothly when conducted on small scale (~15 mg). In total, the synthesis required 13 steps from commercial starting material, and ~15 mg of [(–)-presilphiperfolan-8-ol] has been prepared with spectral properties and optical rotations matching that of the natural isolate.”