Multi-step reaction with 11 steps
1.1: pyridine / 5.5 h / 20 °C / Inert atmosphere
2.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.1: dmap / dichloromethane / 5 h / 20 °C / Inert atmosphere
4.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 15 h / 0 °C / Inert atmosphere
5.1: pyridine; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere
6.1: sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2 h / 0 °C / Inert atmosphere
7.1: trifluoroacetic anhydride / nitromethane / 2.5 h / 80 °C / Inert atmosphere; Molecular sieve
7.2: 2 h / 20 °C / Inert atmosphere
8.1: 1H-imidazole; dmap / dichloromethane / 20 h / 20 °C / Inert atmosphere
9.1: trifluoroacetic acid / water; isopropyl alcohol / 62 h / 20 °C / Inert atmosphere
10.1: ammonium cerium (IV) nitrate / acetonitrile / 1 h / 0 °C / pH 7 / Inert atmosphere; aq. buffer
11.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; dmap; sodium chlorite; disodium hydrogenphosphate; ammonium cerium (IV) nitrate; 2-methyl-but-2-ene; lithium triethylborohydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride;
In
tetrahydrofuran; nitromethane; dichloromethane; water; isopropyl alcohol; acetonitrile; tert-butyl alcohol;
7.1: Friedel Crafts acylation;
DOI:10.1002/anie.201104504