Multi-step reaction with 13 steps
1: LiAlH4
2: pyridinium chlorochromate / CH2Cl2
4: propionic acid
5: 66 percent / AD-mix-β, methanesulfonamide / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C
6: 98 percent / TsOH / acetone / 1 h / 0 - 25 °C
7: 97 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 88 percent / K2CO3 / 1 h / Ambient temperature
9: 75 percent / BF3*Et2O / CH2Cl2
10: diisobutylaluminum hydride / tetrahydrofuran / 1 h / -50 °C
11: 1.) potassium tert-butoxide / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h
12: 70 percent / Pd(PPh3)4, Et3N, CuI / tetrahydrofuran / 2 h / 50 °C
13: 95 percent / RhCl(PPh3)3, H2 / benzene; acetone / 16 h / 760 Torr
With
dmap; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); methanesulfonamide; RhCl(PPh3)3; AD-mix-β; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; pyridinium chlorochromate;
In
tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/ja00064a060