Multi-step reaction with 14 steps
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, 0.5 h
2: 1.) NaHMDS / 1.) THF, 0 deg C, 10 min, 2.) 0.5 h
3: 100 percent / H2, Na2CO3 / 10percent Pd/C / ethyl acetate / 12 h / 25 °C
4: 97 percent / CSA / CH2Cl2; methanol / 1 h / 0 °C
5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, 0.5 h
6: NaClO2, NaH2PO4, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h / 25 °C
7: 91 percent / TBAF / tetrahydrofuran / 8 h / 65 °C
8: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) DMAP / 1.) THF, 0 deg C, 2 h, 2.) THF, C6H6, 80 deg C, 1 h
9: 1.) LiHMDS, HMPA / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C to 25 deg C
10: 1.) t-BuLi, 2.) (2-thiophene)Cu(CN)Li, HMPA
11: 100 percent / PPTS / 1,2-dimethoxy-ethane; H2O / 25 °C
12: 1.) BH3*THF, 2.) 3 N NaOH, 30percent H2O2 / 1.) 0 deg C
13: 82 percent / LiOH / 1,2-dimethoxy-ethane; H2O / 25 °C
14: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) DMAP / 1.) THF, 0 deg C, 2 h, 2.) THF, C6H6, 80 deg C, 1 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium carbonate; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja00108a051