Multi-step reaction with 25 steps
1.1: 81 percent / n-BuLi; BF3*OEt2 / tetrahydrofuran / -78 °C
2.1: 88 percent / TEA; DMAP / CH2Cl2 / 0 °C
3.1: TBAF / tetrahydrofuran
3.2: 91 percent / K2CO3 / methanol
4.1: 89 percent / aq. AcOH
5.1: 99 percent / H2; quinoline / Lindlar catalyst / ethyl acetate
6.1: 97 percent / TEA; DMAP / CH2Cl2
7.1: Eu(fod)3 / toluene / 120 °C
7.2: 70 percent / AcOH; H2O / tetrahydrofuran
8.1: 95 percent / DDQ; 4 Angstroem molecular sieves / CH2Cl2 / 0 °C
9.1: 96 percent / 2,6-lutidine / CH2Cl2 / 0 °C
10.1: 58 percent / CF3CO2H / methanol
11.1: 99 percent / PPTS / CH2Cl2
12.1: 98 percent / mCPBA; NaHCO3 / CH2Cl2 / 0 °C
13.1: (PhSe)2; NaBH4 / ethanol; butan-1-ol / Heating
13.2: H2O2; pyridine; 2-methyl-2-butene / CH2Cl2
14.1: 85 percent / mCPBA; NaHCO3 / CH2Cl2 / 0 °C
15.1: 92 percent / TEA; DMAP / CH2Cl2 / 0 °C
16.1: (PhSe)2; NaBH4 / ethanol; butan-1-ol / 80 °C
16.2: H2O2; pyridine; 2-nethyl-2-butene / CH2Cl2
17.1: 75 percent / DIBAL; n-BuLi / toluene / 0 °C
18.1: 100 percent / TBAF / tetrahydrofuran
19.1: 97 percent / imidazole / dimethylformamide
20.1: 97 percent / CBr4; P(oct)3; TEA / 1-methyl-1-cyclohexene / toluene / 90 °C
21.1: 100 percent / Bu3SnH; AIBN / toluene / 0 °C / Irradiation
22.1: 78 percent / CSA; (HOCH2)2 / methanol
23.1: 100 percent / CSA / 1,2-dichloro-ethane
24.1: 97 percent / DIBAL / toluene / -10 °C
25.1: TEA; DMAP / CH2Cl2
With
1H-imidazole; 2,6-dimethylpyridine; quinoline; dmap; sodium tetrahydroborate; n-butyllithium; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; TOP; 4 A molecular sieve; TEA; diphenyl diselenide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ethylene glycol; acetic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Eu(fod)3;
Lindlar's catalyst; 1-methylcyclohex-1-ene;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; butan-1-ol;
1.1: Yamaguchi reaction;
DOI:10.1016/j.tetlet.2006.11.080