Multi-step reaction with 12 steps
1.1: 98 percent / H2 / Pd/C / ethyl acetate / 12 h / 760.05 Torr
2.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
3.1: 84 percent / Jones reagent / acetone / 0.5 h / 20 °C
4.1: 78 percent / SmI2; MeOH / tetrahydrofuran / -78 - 20 °C
5.1: 91 percent / DIPEA / CH2Cl2 / 17 h / 0 - 20 °C
6.1: 100 percent / p-TsOH*H2O / benzene / 15 h / Heating
7.1: Na; naphthalene / 1,2-dimethoxy-ethane / 0.25 h / -78 °C
8.1: 1.2 g / DMAP / acetonitrile / 0 - 20 °C
9.1: NaNO2; CuCl; HCl / methanol / 0.25 h / 20 °C
9.2: allyltrimethylsilane; BF3*Et2O / tetrahydrofuran; diethyl ether / -78 - -5 °C
10.1: 180 mg / Et3N / CH2Cl2 / 14 h / Heating
11.1: BH3*THF; 2-methyl-2-butene / tetrahydrofuran; diethyl ether / 0 - 20 °C
11.2: H2O2; aq. NaOH / tetrahydrofuran; diethyl ether / 0.83 h / 20 °C
12.1: 164 mg / Et3N; DMAP / CH2Cl2 / 0 - 20 °C
With
hydrogenchloride; methanol; dmap; jones reagent; samarium diiodide; borane-THF; 2-methyl-but-2-ene; naphthalene; tetrabutyl ammonium fluoride; hydrogen; sodium; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; copper(l) chloride; sodium nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; ethyl acetate; acetone; acetonitrile; benzene;
1.1: Catalytic hydrogenation / 2.1: desilylation / 3.1: Oxidation / 4.1: Cyclization / 5.1: Condensation / 6.1: cyclocondensation / 7.1: Reduction / 8.1: Acylation / 9.1: Oxidation / 9.2: Substitution / 10.1: Acylation / 11.1: hydroboration / 11.2: Oxidation / 12.1: Tosylation;
DOI:10.1021/jo000260z