Multi-step reaction with 8 steps
1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 0.5 h / 110 °C / Inert atmosphere
2.1: polymethylhydrosiloxane / toluene / 12 h / 130 °C / Inert atmosphere
3.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / toluene; tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / toluene / 12 h / 70 °C / Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C / Inert atmosphere
5.2: 1 h / -78 °C / Inert atmosphere
6.1: boron trifluoride diethyl etherate; sodium cyanoborohydride / dichloromethane; acetonitrile / 1 h / -78 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 25 °C / Inert atmosphere
8.1: 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
8.2: 1 h / 0 - 25 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium cyanoborohydride; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane; toluene; acetonitrile; pentane;
1.1: |Cross Metathesis / 3.1: |Corey-Bakshi-Shibata Reduction;
DOI:10.1021/acs.jmedchem.0c00151