Multi-step reaction with 14 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C
1.2: 2 h / 0 - 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / -78 °C
2.2: -78 °C
3.1: magnesium / diethyl ether / Reflux
3.2: 2 h / -78 - 20 °C
3.3: Cooling
4.1: chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II); potassium tert-butylate; sodium carbonate / toluene / 6 h / 20 °C / Inert atmosphere
5.1: methanol; potassium carbonate / 2 h / 20 °C
6.1: 1H-imidazole / dichloromethane / 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
8.2: -78 - 20 °C
9.1: sodium hydride / diethyl ether; mineral oil / 0.17 h / -5 °C
9.2: 4 h / -5 - 20 °C
10.1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol
11.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C
12.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C
13.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / dichloromethane / 72 h / -78 - -20 °C / Molecular sieve
13.2: 1 h
14.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
With
1H-imidazole; titanium(IV) isopropylate; methanol; chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II); oxalyl dichloride; methanesulfonamide; AD-mix-β; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol;
2.1: Swern oxidation / 2.2: Swern oxidation / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.2: Horner-Wadsworth-Emmons olefination / 10.1: Sharpless dihydroxylation / 13.1: Keck allylation;
DOI:10.1016/j.tetasy.2012.05.017