Multi-step reaction with 14 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 4 h / -5 - 0 °C / Inert atmosphere
2.1: 2,6-di-tert-butyl-4-methyl-phenol / tert-butylbenzene / 27 h / 180 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine; sodium iodide / 1,2-dichloro-ethane / 3 h / 40 °C / Inert atmosphere
4.1: methanesulfonamide; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] / water; tert-butyl alcohol / 62 h / 0 °C / Inert atmosphere
5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.83 h / 20 °C / Inert atmosphere
7.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C / Inert atmosphere
8.1: magnesium bromide ethyl etherate / dichloromethane / 40 h / -10 °C / Inert atmosphere
9.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C / Inert atmosphere
10.1: hydrogenchloride; water / methanol / 16 h / 20 °C
11.1: triethylamine / dichloromethane / 0.5 h / 0 °C
12.1: sodium hydroxide / ethanol; water / 1 h / 80 °C
13.1: sodium hydroxide / water; ethyl acetate / 1.33 h / 0 - 20 °C
14.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
14.2: 1 h / 20 °C / Inert atmosphere
With
hydrogenchloride; oxalyl dichloride; methanesulfonamide; 2,6-di-tert-butyl-4-methyl-phenol; water; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium bromide ethyl etherate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; sodium hydroxide;
In
tetrahydrofuran; methanol; tert-butylbenzene; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;
2.1: Overman rearrangement / 4.1: Sharpless dihydroxylation / 7.1: Swern oxidation / 8.1: Hosomi-Sakurai allylation / 14.2: Suzuki-Miyaura coupling;
DOI:10.1021/ol102856j