Multi-step reaction with 15 steps
1.1: mesitylenesulfonylhydroxylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
2.1: ozone / dichloromethane; isopropyl alcohol / 0.17 h / -78 °C / Inert atmosphere
2.2: 0.75 h / -78 - 0 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran / Reflux; Inert atmosphere
4.1: lithium borohydride / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere
6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0 °C / Inert atmosphere
7.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 20 °C / Inert atmosphere
8.1: triethylamine; lithium chloride / tetrahydrofuran / 30 °C / Inert atmosphere
9.1: acetic acid; hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol / 25 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / ethanol / 25 °C / Inert atmosphere
12.1: ortho-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere
12.2: 20 °C / Inert atmosphere
13.1: sodium tetrahydroborate / ethanol / 20 °C / Inert atmosphere
14.1: potassium carbonate / acetonitrile / 90 °C / Inert atmosphere
15.1: Hoveyda-Grubbs catalyst second generation / toluene / 60 °C / Inert atmosphere
With
dmap; sodium tetrahydroborate; lithium borohydride; Hoveyda-Grubbs catalyst second generation; ortho-nitrophenyl selenocyanate; ammonium cerium (IV) nitrate; tributylphosphine; 10 wt% Pd(OH)2 on carbon; hydrogen; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; mesitylenesulfonylhydroxylamine; sodium hydride; potassium carbonate; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride;
In
tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; toluene; acetonitrile;
2.2: |Clemmensen Reduction / 7.1: |Parikh-Doering Oxidation;
DOI:10.1002/asia.201301248