Multi-step reaction with 14 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 19 h / -78 - 20 °C
1.3: 21 h / -78 - 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C
2.2: 21 h / 20 °C
3.1: barium hydroxide octahydrate / tetrahydrofuran; water / 60 h / 20 °C
4.1: 4-methyl-morpholine; methyl chloroformate / tetrahydrofuran / 0.5 h / -10 °C
4.2: 0.5 h / 0 °C
5.1: dmap; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C
6.1: acetone; acetonitrile / 2 h / Irradiation
6.2: 16 h / 20 °C / 760.05 Torr
7.1: t-butyldimethylsiyl triflate / hexane; dichloromethane / 12 h / 0 °C / Molecular sieve
8.1: tetrahydrofuran; diethyl ether / -78 °C
9.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C
10.1: dmap; triethylamine / 18 h / 20 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
12.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 4 h / 20 °C
13.1: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / ethanol / 4 h / 20 °C / 760.05 Torr
14.1: pyridine / 20 °C
With
4-methyl-morpholine; pyridine; dmap; barium hydroxide octahydrate; 20 wt.% Pd(OH)2 on activated carbon; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; methyl chloroformate; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;
DOI:10.1002/anie.201106889