Multi-step reaction with 14 steps
1.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C
1.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C
2.1: Mg; iodine / diethyl ether
2.2: 88 percent / diethyl ether / 3 h / 20 °C
3.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C
4.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C
4.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C
5.1: 90 percent / tetrahydrofuran / 2 h / sonication
6.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C
7.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C
8.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling
9.1: 28 percent / propionic acid / 48 h / 180 °C
10.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C
11.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr
12.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C
13.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C
14.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; iodine; silica gel; sodium hydride; sodium hydrogencarbonate; ozone; magnesium; propionic acid; pyridinium chlorochromate;
palladium on activated charcoal; Wilkinson's catalyst; Grubbs catalyst first generation; Lindlar's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
2.2: Grignard reaction / 9.1: Claisen orthoester rearrangement;
DOI:10.1016/j.tet.2006.01.021