Multi-step reaction with 12 steps
1.1: phosphorus tribromide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
4.1: methanol / 16 h / 55 °C / Inert atmosphere; Molecular sieve
5.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere
5.2: 12 h / Inert atmosphere; Reflux
6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 8.5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
7.1: pyridine hydrogenfluoride; pyridine / acetonitrile / 2.5 h / 0 - 20 °C / Inert atmosphere
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
8.2: 1 h / -78 - 20 °C / Inert atmosphere
9.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide; dmap / dichloromethane / 8.5 h / 0 °C / Inert atmosphere; Reflux
11.1: Schwartz's reagent / toluene / 6 h / 50 °C / Inert atmosphere
11.2: -78 - 0 °C / Inert atmosphere
11.3: 1 h / 0 °C / Inert atmosphere
12.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; dmap; Schwartz's reagent; oxalyl dichloride; boron trifluoride diethyl etherate; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
8.1: |Swern Oxidation / 8.2: |Swern Oxidation;
DOI:10.1016/j.tet.2014.03.020