Multi-step reaction with 14 steps
1.1: 0.543 g / pyridine / CH2Cl2
2.1: 93 percent / 4-dimethylaminopyridine / pyridine / CH2Cl2 / 0 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 0.929 g / NaN3 / dimethylformamide / 5 h / 60 °C
5.1: H2 / PtO2 / ethyl acetate
6.1: 1.96 g / triethylamine / CH2Cl2 / 20 °C
7.1: 97 percent / H2 / Pd/C / ethanol
8.1: 82 percent / oxalyl chloride; methyl sulfoxide; Et3N / CH2Cl2 / -78 - 20 °C
9.1: potassium 1,1,1,3,3,3-hexamethyldisilylamide / tetrahydrofuran / 1 h / -78 °C
9.2: 94 percent / tetrahydrofuran / -78 - 20 °C
10.1: 82 percent / pyridine; HF / 3 h / 0 °C
11.1: 72 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; NaClO2; NaClO / acetonitrile; aq. phosphate buffer / 35 °C / pH 6.85
12.1: diisopropylethylamine; 1-hydroxybenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide / CH2Cl2 / 0.33 h / 0 °C
12.2: 72 percent / CH2Cl2 / 16 h / 0 - 20 °C
13.1: trifluoroacetic acid / CH2Cl2 / 5 h
With
pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium azide; oxalyl dichloride; free radical; hydrogen fluoride; hydrogen; benzotriazol-1-ol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
pyridine; platinum(IV) oxide; palladium on activated charcoal;
In
tetrahydrofuran; phosphate buffer; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
9.1: Swern oxidation;
DOI:10.1021/ja0686256