Multi-step reaction with 12 steps
1.1: trifluoroacetic acid / benzene / 0.5 h / Heating
2.1: LiHMDS; Me3SiCl; Et3N / hexane; tetrahydrofuran / 2 h / -78 °C
2.2: HCl / H2O / pH 2
3.1: 95 percent / DMAP; DIC; TFA / CH2Cl2 / 40 °C
4.1: 82 percent / BF3-Et2O; Me2S / CH2Cl2 / 0.17 h / 0 °C
5.1: 96 percent / imidazole / dimethylformamide / 8 h / 20 °C
6.1: 100 percent / lithium hydroxide / 2-methyl-propan-2-ol; H2O / 2 h
7.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 3 h
7.2: 89 percent / DMAP / benzene / 2 h
8.1: 95 percent / HF / H2O; acetonitrile / 0.5 h / 0 °C
9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 3 h
9.2: 92 percent / DMAP; Et3N / benzene / 2 h
10.1: 95 percent / HF / H2O; acetonitrile / 0.5 h / 0 °C
11.1: 95 percent / phosphate buffer; zinc dust / H2O; tetrahydrofuran / 4 h
12.1: 76 percent / DMAP; DMAP-TFA; DIC / CHCl3 / 9 h / Heating
With
1H-imidazole; dmap; lithium hydroxide; chloro-trimethyl-silane; phosphate buffer; dimethylsulfide; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; hydrogen fluoride; dacarbazine; 4-N,N-dimethylaminopyridine trifluoroacetate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; zinc;
In
tetrahydrofuran; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
1.1: Cyclization / 2.1: Rearrangement / 2.2: Hydrolysis / 3.1: Esterification / 4.1: Hydrolysis / 5.1: Etherification / 6.1: Hydrolysis / 7.1: Substitution / 7.2: Substitution / 8.1: Hydrolysis / 9.1: Substitution / 9.2: Substitution / 10.1: Hydrolysis / 11.1: Reduction / 12.1: Cyclization;
DOI:10.1021/jo991681n