Multi-step reaction with 18 steps
1.1: 100 percent / TEA; DMAP / CH2Cl2
2.1: 94 percent / AcOH; H2O / tetrahydrofuran / 50 °C
3.1: 98 percent / K2CO3 / methanol; CH2Cl2
4.1: 99 percent / MeI; NaHCO3 / H2O; acetone / 40 °C
5.1: 99 percent / H2; quinoline / Lindlar cat. / ethyl acetate
6.1: 65 percent / Eu(fod)3 / xylene / 120 °C
7.1: 99 percent / AgNO3; pyridine / acetonitrile
8.1: 94 percent / MCPBA; NaHCO3 / CH2Cl2; H2O / 0 °C
9.1: (PhSe)2; NaBH4 / ethanol; butan-1-ol / Heating
9.2: 62 percent / H2O2; pyridine; 2-methyl-2-butene / CH2Cl2
10.1: 86 percent / MCPBA / CH2Cl2 / 0 °C
11.1: 97 percent / DMAP; TEA / CH2Cl2
12.1: (PhSe)2; NaBH4 / ethanol; butan-1-ol / 50 °C
12.2: 38 percent / H2O2; pyridine; 2-methyl-2-butene / CH2Cl2
13.1: 59 percent / n-BuLi; DIBAL / toluene
14.1: 98 percent / TEA; DMAP / CH2Cl2
15.1: 93 percent / AcOH; H2O / tetrahydrofuran
16.1: pyridine / CH2Cl2
17.1: n-Bu4NBr / toluene / 50 °C
18.1: 74 percent / Bu3SnH; Et3B / toluene / 0 °C
With
pyridine; quinoline; dmap; sodium tetrahydroborate; n-butyllithium; triethyl borane; TEA; diphenyl diselenide; tetrabutylammomium bromide; water; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; silver nitrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; Eu(fod)3; methyl iodide;
Lindlar catalyst;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; xylene; butan-1-ol;
DOI:10.1246/cl.2007.278