Actidione synthesis

Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: lithium chloride; triethylamine; pivaloyl chloride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere
2.2: 1 h / -78 - 0 °C / Inert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
4.2: 1 h / -78 - 0 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; triethylsilane / acetone / 20 °C / Inert atmosphere
6.1: toluene / 72 h / 20 °C / Inert atmosphere
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 2 h / 60 °C / Inert atmosphere
8.1: Crabtree's catalyst; hydrogen / dichloromethane / 2 h / 20 °C / 760.05 Torr
9.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 1 h / 20 °C / Inert atmosphere

References:

Park, Yongho;Koga, Yumi;Su, Cindy;Waterbury, Amanda L.;Johnny, Christopher L.;Liau, Brian B. [Angewandte Chemie - International Edition,2019,vol. 58,# 16,p. 5387 - 5391][Angew. Chem.,2019,vol. 131,p. 5441 - 5445,5]