Multi-step reaction with 20 steps
1.1: n-Bu3P / tetrahydrofuran / 20 °C
2.1: H2O2 / tetrahydrofuran; H2O / 0 - 20 °C
3.1: dimethylformamide; tetrahydrofuran / 0 °C
4.1: 96 percent / (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 20 °C
5.1: TFA / tetrahydrofuran / 20 °C
5.2: 98 percent / imidazole / dimethylformamide / 20 °C
6.1: m-CPBA; NaHCO3 / CH2Cl2 / 0 - 20 °C
7.1: LiAlH4 / diethyl ether / -20 °C
8.1: TBAI; NaH / tetrahydrofuran; dimethylformamide / 20 °C
8.2: 51 percent / CSA / methanol; tetrahydrofuran / 0 °C
9.1: 95 percent / iodine; PPh3; imidazole / tetrahydrofuran / 20 °C
10.1: 90 percent / dimethylsulfoxide / 45 °C
11.1: DIBAL-H / CH2Cl2 / -95 °C
11.2: 83 percent / NaBH4 / CH2Cl2; methanol / -20 - 20 °C
12.1: 95 percent / nBu3P; pyridine / 20 °C
13.1: NCS / CH2Cl2; CCl4 / 20 °C
14.1: 70 percent / AgOTf; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem MS / CH2Cl2; CCl4 / -90 - -15 °C
15.1: 93 percent / AgOTf; i-Pr2NEt; 4 Angstroem MS / benzene / 20 °C
16.1: LiOH*H2O / dioxane; H2O / 20 °C
17.1: n-Bu3P / dimethylformamide / 20 °C
18.1: 63 percent / n-Bu3GeH; Et3B / benzene
19.1: 52 percent / LiN(TMS)2 / tetrahydrofuran / -95 °C
20.1: 83 percent / Pd(OAc)2 / acetonitrile / 20 °C
With
pyridine; 1H-imidazole; lithium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; triethyl borane; tributylphosphine; 4 Angstroem MS; dihydrogen peroxide; iodine; silver trifluoromethanesulfonate; tributylgermanium hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane;
palladium diacetate; Grubbs catalyst first generation;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
20.1: Saegusa oxidation;
DOI:10.1016/j.tetlet.2007.01.102