Multi-step reaction with 14 steps
1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.5 h / -78 °C
1.2: 5 h / -78 °C
2.1: tetrabutyl ammonium fluoride; ammonium chloride / tetrahydrofuran; water / 0.5 h / 20 °C
3.1: methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate / 1 h / 0 - 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
4.2: 3 h / 0 - 20 °C
5.1: hydrogenchloride / methanol / 25 °C
6.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C
7.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C
8.1: lithium hydroxide / methanol / 2 h / 25 °C
9.1: pyridine; diethylamino-sulfur trifluoride / dichloromethane / 12 h / 20 °C / Inert atmosphere
10.1: sodium periodate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / methanol / 2 h / 0 °C
11.1: methanol; sodium tetrahydroborate / 1 h / 0 °C
12.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C
13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C
13.2: 20 °C
14.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 24 h / -40 - 60 °C
With
pyridine; 1H-imidazole; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; diethylamino-sulfur trifluoride; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; sodium hydride; ammonium chloride; 4-methylmorpholine N-oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
7.1: Mitsunobu reaction / 14.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2012.03.023