Multi-step reaction with 15 steps
1.1: toluene-4-sulfonic acid / benzene / Reflux
2.1: n-butyllithium / tetrahydrofuran / -78 °C
2.2: -78 - 20 °C
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether / 20 °C
3.2: 0 °C
3.3: -78 °C
4.1: 1H-imidazole / dichloromethane / 20 °C
5.1: tetrakis(triphenylphosphine) palladium(0); triethylamine / 60 °C
6.1: diisobutylaluminium hydride / dichloromethane / -78 °C
7.1: hydrogenchloride; water / tetrahydrofuran / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 50 °C
9.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C
9.2: -78 °C
10.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 50 °C
11.1: pyridine hydrofluoride / tetrahydrofuran / 0 °C
12.1: pig liver esterase; water / dimethyl sulfoxide / 17 h / 30 °C / pH 8 / aq. phosphate buffer; Enzymatic reaction
13.1: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 20 °C / High dilution conditions
14.1: hydrogenchloride; water / tetrahydrofuran / 45 °C
15.1: Dess-Martin periodane / dichloromethane / 20 °C
With
1H-imidazole; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; pig liver esterase; pyridine hydrofluoride; 2-methyl-6-nitrobenzoic anhydride; water; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene;
15.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2012.01.058