Multi-step reaction with 20 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
15: 1.) LiHMDS, HMPA / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C to 25 deg C
16: 66 percent / CrCl2, NiCl2 / dimethylformamide / 3 h / 25 °C / Irradiation
17: 89 percent / 1.) KH / diethyl ether / 25 °C
18: 67 percent / n-Bu3SnH, AIBN / benzene / 80 °C
19: 1.) BH3*THF, 2.) 3 N NaOH, 30percent H2O2 / 1.) -30 deg C
20: 96 percent / 2,6-lutidine / CH2Cl2 / 1 h / -70 °C
With
2,6-dimethylpyridine; chromium dichloride; 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; 2,2'-azobis(isobutyronitrile); 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hydride; sodium carbonate; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; nickel dichloride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ja00108a051