Multi-step reaction with 10 steps
1.1: 100 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 0 °C
2.1: LiN[Si(CH3)3]2 / tetrahydrofuran / -78 °C
2.2: 30 percent / tetrahydrofuran / -78 - 20 °C
3.1: (PhCH2)(Cl)Pd(PPh3)2; LiCl; aq. Na2CO3 / 1,2-dimethoxy-ethane / 86 °C
4.1: 100 percent / H2 / 5 percent Pd/C / ethyl acetate
5.1: aq. LiOH / dioxane / 0 - 20 °C
6.1: 94 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt*H2O; N-methylmorpholine / dimethylformamide
7.1: 100 percent / Et3SiH / CH2Cl2 / 0 °C
8.1: 70 percent / NaI; iPr2NEt / dimethylsulfoxide
9.1: 100 percent / aq. LiOH / tetrahydrofuran / 0 °C
10.1: aq. AcOH / dimethylformamide / 0 °C
With
4-methyl-morpholine; triethylsilane; lithium hydroxide; oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); hydrogen; sodium carbonate; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium chloride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
1.1: Oxidation / 2.1: Enolization / 2.2: Triflation / 3.1: Arylation / 4.1: Catalytic hydrogenation / 5.1: Hydrolysis / 6.1: Acylation / 7.1: Acidolysis / 8.1: Alkylation / 9.1: Hydrolysis / 10.1: Thioacylation;
DOI:10.1248/cpb.48.740