Multi-step reaction with 9 steps
1.1: 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: 64 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: NaBH4 / methanol / 2 h
6.1: 92 percent / imidazole / CH2Cl2 / 3 h / 20 °C
7.1: mCPBA / CH2Cl2 / 0.5 h / -78 °C
8.1: hexamethyldisilazane / acetonitrile / Heating
8.2: Et3N; TMSOTf; ZnI2 / toluene / 0 °C
9.1: Et3N; 2,4,6-triisopropylbenzenesulfonyl chloride; DMAP / acetonitrile / 20 °C
9.2: 75 percent / aq. NH3 / acetonitrile / 3 h
With
1H-imidazole; dmap; 2,4,6-triisopropylphenylsulfonyl chloride; oxalyl dichloride; dimethylsulfide borane complex; titanocene dichloride; sodium methylate; acetic anhydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;
1.1: Moffatt oxidation / 4.1: Swern oxidation;
DOI:10.1021/jm050912h