Multi-step reaction with 16 steps
1.1: Amberlyst 15 / acetone / 48 h / 20 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 96 h / 20 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C
4.1: triethylamine / N,N-dimethyl-formamide / 43 h / 130 °C
5.1: 3,3-dimethyldioxirane / dichloromethane / -78 - 20 °C
6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -13 - -12 °C
7.2: 13 / 0.5 h / -95 - -90 °C
8.1: oxygen; ozone / dichloromethane / -78 °C
9.1: diisopropylamine / dichloromethane / -78 - 20 °C
10.1: zinc borohydride / diethyl ether / 0.5 h / -29 °C
10.2: tetrabutylammonium fluoride / 2; 13 / 0.5 h / 20 °C
11.1: sodium hydrogencarbonate / toluene / 42 h / 80 °C
12.1: n-butanethiol; potassium carbonate; magnesium bromide / diethyl ether / 0.5 h / 20 °C
13.1: dmap / dichloromethane / 1 h / 20 °C
14.1: toluene-4-sulfonic acid / 1.75 h / 20 °C
15.1: hydrogenchloride / methanol / 0.75 h / 45 °C
16.1: dichloromethane / 1.25 h / 20 °C
With
hydrogenchloride; dmap; Amberlyst 15; n-butanethiol; zinc borohydride; tetrabutyl ammonium fluoride; oxygen; 3,3-dimethyldioxirane; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; magnesium bromide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/chem.200700302