Multi-step reaction with 20 steps
1.1: camphor-10-sulfonic acid; orthoformic acid triethyl ester / dichloromethane / 72 h / 0 °C / Inert atmosphere
2.1: sodium hydride / mineral oil; tetrahydrofuran / 16 h / Inert atmosphere; Reflux
2.2: 0 °C
3.1: sodium hydride / mineral oil; diethyl ether / 1.5 h / 0 °C / Inert atmosphere
3.2: 6.5 h / 0 °C / Inert atmosphere
4.1: copper(l) cyanide / diethyl ether / 0.17 h / -50 °C / Inert atmosphere
4.2: 16 h / -35 - 20 °C / Inert atmosphere
5.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere
5.2: 1 h / -78 °C / Inert atmosphere
5.3: 21 h / -78 - 20 °C / Inert atmosphere
6.1: caesium carbonate / methanol; tetrahydrofuran / 16 h / 65 °C / Inert atmosphere
6.2: 0.33 h / 0 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / 1,4-dioxane / 0.47 h / 100 °C / Inert atmosphere
8.1: magnesium / tetrahydrofuran; ethylene dibromide / 2.5 h / Inert atmosphere; Reflux
8.2: 16.75 h / -78 - 20 °C / Inert atmosphere
9.1: L-Selectride / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere
9.2: 0.33 h / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / N,N-dimethyl-formamide / 1 h / 150 °C / Inert atmosphere
11.1: dihydrogen peroxide; peracetic acid; sodium carbonate / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
11.2: 0.33 h / 0 °C / Inert atmosphere
12.1: water / 48 h / 100 °C / Inert atmosphere; Sealed tube
12.2: 20 °C / Inert atmosphere; Sealed tube
13.1: sulfuric acid / 44 h / Inert atmosphere; Reflux
14.1: triethylaluminum / tetrahydrofuran; toluene / 0.33 h / -78 °C / Inert atmosphere
14.2: 1.33 h / 0 - 20 °C / Inert atmosphere
14.3: 0.33 h / Inert atmosphere
15.1: pyridinium p-toluenesulfonate / dichloromethane / 0.33 h / 20 °C / Inert atmosphere
15.2: 18 h / 20 °C / Inert atmosphere
16.1: acetic acid / dichloromethane / 72 h / 20 °C / Inert atmosphere
17.1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 72 h / 80 °C / Inert atmosphere
18.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 48 h / 20 °C / Inert atmosphere
19.1: 2-bromopyridine-N-oxide; C18H15AuP(1+)*C2F6NO4S2(1-)*C7H8 / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere
20.1: diethylzinc; (1S,2S)-N-Methylpseudoephedrine; oxygen / toluene / 16 h / 0 - 20 °C / Inert atmosphere
With
2-bromopyridine-N-oxide; peracetic acid; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; sulfuric acid; camphor-10-sulfonic acid; C18H15AuP(1+)*C2F6NO4S2(1-)*C7H8; (1S,2S)-N-Methylpseudoephedrine; tetrabutyl ammonium fluoride; dihydrogen peroxide; diethylzinc; oxygen; triethylaluminum; copper(l) cyanide; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; sodium carbonate; caesium carbonate; magnesium; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; orthoformic acid triethyl ester;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; ethylene dibromide; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/ja405547f