Multi-step reaction with 11 steps
1.1: ozone; Ph3P / CH2Cl2 / -78 °C
1.2: 65 percent / CuI; n-Bu3P; BuLi / diethyl ether; tetrahydrofuran; hexane / 2 h / -78 °C
2.1: trifluoroacetic acid / benzene / 0.5 h / Heating
2.2: LiHMDS; Me3SiCl; Et3N / tetrahydrofuran / -78 °C
2.3: 89 percent / HCl / H2O / pH 2
3.1: 92 percent / DMAP; DIC; TFA / CH2Cl2 / 40 °C
4.1: 82 percent / DDQ / H2O; CH2Cl2 / 1 h
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: 92 percent / DMAP / benzene / 2 h
8.1: 100 percent / HF / H2O; acetonitrile / 0.5 h / 0 °C
9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 3 h
9.2: 95 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
With
1H-imidazole; dmap; lithium hydroxide; phosphate buffer; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; ozone; dacarbazine; triethylamine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
1.1: Oxidation / 1.2: Addition / 2.1: Cyclization / 2.2: Rearrangement / 2.3: 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;
DOI:10.1021/jo991681n