Multi-step reaction with 8 steps
1: 100 percent / H2, conc. HCl / Pt/C / H2O / 264 h / Ambient temperature
2: 98 percent / 4M NaOH / Ambient temperature
3: (COCl)2, DMSO, Et3N / tetrahydrofuran / 0.5 h / -35 - 20 °C
4: 1.) nBuLi / 1.) THF, hexane, room temperature, 30 min, 2.) -78 deg C -> room temperature, 1 h
5: I2 / CHCl3 / 192 h / Irradiation
6: 72 percent / Ad-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 7 h, 2.) room temperature, 17 h
7: 1.) CH3C(OCH3)3, TMSCL, 2.) K2CO3 / 1.) CH2Cl2, room temperature, 3 h, 2.) MeOH, room temperature, 1 h
8: MeLi / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C
With
hydrogenchloride; Trimethyl orthoacetate; sodium hydroxide; AD-mix-α; n-butyllithium; chloro-trimethyl-silane; oxalyl dichloride; methanesulfonamide; methyllithium; hydrogen; iodine; potassium carbonate; dimethyl sulfoxide; triethylamine;
platinum on activated charcoal;
In
tetrahydrofuran; diethyl ether; chloroform; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(99)00050-2