Multi-step reaction with 16 steps
1.1: acetonitrile; tert-butyl alcohol; aq. phosphate buffer / 2 h / 0 - 20 °C
1.2: 20 °C
2.1: tert.-butylhydroperoxide / ethyl acetate / 0.33 h / 20 °C / Molecular sieve
2.2: 48 h / Molecular sieve
3.1: chloroform / 5 h / 60 °C
4.1: benzo[1,3,2]dioxaborole / 2 h / 0 - 20 °C
4.2: 1 h / 0 °C / Reflux
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C
5.2: 1 h / 0 °C
5.3: 2 h / 0 - 20 °C
6.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
6.2: 5 h / 0 - 20 °C
6.3: 0.5 h / 0 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / chloroform / 12 h / Reflux
8.1: tetrahydrofuran / 0.5 h / 0 °C
9.1: trichloroacetic acid / dichloromethane / 1 h / 20 °C
9.2: Reflux
10.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C
11.1: lithium diisopropyl amide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 1 h / -78 °C
12.1: triethylamine; dmap / dichloromethane / 0.5 h / 0 °C
13.1: magnesium monoperoxyphthalate / dichloromethane / 0.5 h / 20 °C
14.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; samarium diiodide / methanol; tetrahydrofuran / 0.17 h / 0 °C
15.1: oxygen; 5,15,10,20-tetraphenylporphyrin / acetonitrile / 0 °C / Irradiation
16.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 16 h / 50 °C / Sealed tube
16.2: 12 h / 8 °C
With
tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; n-butyllithium; samarium diiodide; boron trifluoride diethyl etherate; magnesium monoperoxyphthalate; oxygen; 5,15,10,20-tetraphenylporphyrin; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; trichloroacetic acid; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; aq. phosphate buffer; dichloromethane; chloroform; ethyl acetate; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja406255j