Multi-step reaction with 14 steps
2.1: 32 percent / K2CO3 / dimethylformamide / 72 h / 80 °C
3.1: 100 percent / K2CO3 / dimethylformamide / 3 h / 0 °C
4.1: 97 percent / DIBAH / CH2Cl2 / 3 h / -78 °C
5.1: 76 percent / PCC / CH2Cl2 / 2 h / 20 °C
6.1: 30 percent aq. hydrogen peroxide; phenylselenic acid / CH2Cl2 / 48 h / 20 °C
6.2: KOH / methanol / 0.5 h / 20 °C
7.1: KOH / dimethylsulfoxide / 3 h / 20 °C
8.1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / methanol / 18 h / 20 °C
9.1: 98 percent / pyridine / diethyl ether / 4 h / 20 °C
10.1: AlCl3 / CH2Cl2 / 3 h / 20 °C
10.2: 94 percent / aq. HCl / methanol / 0.5 h / Heating
11.1: 60 percent / Huenig base / CH2Cl2 / 24 h / 20 °C
12.1: 77 percent / aq. K2CO3; n-Bu3NHSO4 / benzene / 20 h / 20 °C
13.1: NaH / dimethylsulfoxide / 3 h / 20 °C
13.2: aq. oxalic acid / 0 °C
13.3: AcOH; conc. HCl / 1.5 h
14.1: (COCl)2; DIPEA; DMSO / CH2Cl2 / 0.5 h / -78 - 20 °C
With
pyridine; potassium hydroxide; aluminium trichloride; oxalyl dichloride; n-Bu3NHSO4; phenylselenate; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate;
palladium dihydroxide;
In
methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
1.1: Esterification / 2.1: Condensation / 3.1: Methylation / 4.1: Reduction / 5.1: Oxidation / 6.1: Oxidation / 6.2: Hydrolysis / 7.1: Methylation / 8.1: Hydrogenolysis / 9.1: Esterification / 10.1: Rearrangement / 10.2: Hydrolysis / 11.1: Alkylation / 12.1: Condensation / 13.1: Reduction / 13.2: Cyclization / 13.3: desilylation / 14.1: Oxidation;
DOI:10.1016/S0040-4039(00)00812-1