Multi-step reaction with 10 steps
1.1: 92 percent / Ac2O; DMSO / 20 °C
2.1: titanocene dichloride / tetrahydrofuran; diethyl ether / 2 h / 20 °C
2.2: 4.12 g / diethyl ether; tetrahydrofuran / 48 h / Heating
3.1: BH3*SMe2 / tetrahydrofuran / 2.5 h / 0 - 20 °C
3.2: 70 percent / aq. H2O2; NaOH / tetrahydrofuran / 2 h
4.1: oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
5.1: NaOMe / methanol / 16 h
5.2: 1.58 g / NaBH4 / methanol / 2 h
6.1: 90 percent / imidazole / CH2Cl2 / 3 h / 20 °C
7.1: mCPBA / CH2Cl2 / 0.5 h / -78 °C
8.1: hexamethyldisilazane / acetonitrile / 3 h / Heating
8.2: Et3N; TMSOTf; ZnI2 / toluene / 24 h / 0 °C
9.1: NaN3 / dimethylformamide / 16 h / 20 °C
10.1: 0.143 g / H2 / Pd/C / methanol / 48 h
With
1H-imidazole; sodium azide; oxalyl dichloride; dimethylsulfide borane complex; titanocene dichloride; hydrogen; sodium methylate; acetic anhydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
1.1: Moffatt oxidation / 4.1: Swern oxidation;
DOI:10.1021/jm050912h