Multi-step reaction with 16 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 20 °C
2.1: p-toluenesulfonyl chloride; pyridine / 16 h / 0 - 20 °C
2.2: 2 h / 65 °C
2.3: 0.5 h / -78 °C
3.1: dichloromethane / 16 h / 20 °C / Molecular sieve
3.2: 6 h / -78 - 20 °C
4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 40 h / 80 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
7.1: oxalyl dichloride; triethylamine; dimethyl sulfoxide / dichloromethane / 0.25 h / -60 - 20 °C
8.1: dichloromethane / 5 h / 0 - 20 °C
9.1: n-butyllithium; diethylamine / tetrahydrofuran / 2 h / -78 °C
10.1: lithium borohydride / tetrahydrofuran / 16 h / 66 °C
11.1: toluene-4-sulfonic acid / tetrahydrofuran / 16 h / 66 °C
12.1: 20% palladium hydroxide-activated charcoal; hydrogen / 2,2,2-trifluoroethanol / 16 h / 20 °C
13.1: triethylamine / dichloromethane / 16 h / 20 °C
14.1: trimethylaluminum / dichloromethane / 16 h / 20 °C
15.1: sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C
16.1: lithium aluminium tetrahydride / tetrahydrofuran; dichloromethane / 3.5 h / -78 - 10 °C
With
pyridine; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; oxalyl dichloride; 20% palladium hydroxide-activated charcoal; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride;
In
tetrahydrofuran; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; acetonitrile;
3.1: |Pictet-Spengler Synthesis / 3.2: |Pictet-Spengler Synthesis;
DOI:10.1016/j.tetlet.2013.01.074