Multi-step reaction with 18 steps
1.1: sodium hydride / tetrahydrofuran; paraffin oil / 0 °C
1.2: 6 h / 20 °C
2.1: ozone / dichloromethane / 0.25 h / -78 °C
2.2: -78 °C
3.1: sodium tetrahydroborate / methanol / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 0 - 20 °C
5.1: copper(II) choride dihydrate / acetonitrile / 0 - 20 °C
6.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0.5 h / 20 °C
7.1: potassium carbonate / methanol / 1 h / 20 °C
8.1: magnesium / diethyl ether
8.2: 2 h / -40 - 20 °C
9.1: sodium hydride / tetrahydrofuran; paraffin oil / 0.5 h / 0 °C
9.2: 5 h / 20 °C
10.1: ozone / dichloromethane / 0.25 h / -78 °C
10.2: -78 °C
11.1: benzene / 2 h / Reflux
12.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / 0 °C
12.2: 1 h / 20 °C
13.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C
14.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide / dichloromethane / 6 h / -20 - -10 °C / Molecular sieve
14.2: 3 h / -20 - 20 °C
15.1: sodium periodate / water; acetone / 0 - 20 °C
16.1: tetrahydrofuran / 2 h / 20 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
18.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 0 °C
With
1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) choride dihydrate; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; Cumene hydroperoxide; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; magnesium; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; paraffin oil; benzene;
11.1: Wittig reaction / 14.1: Sharpless asymmetric epoxidation;
DOI:10.1016/j.tetasy.2012.02.009
