Multi-step reaction with 11 steps
1: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C
2: 82 percent / DIBAL / toluene / 1 h / -78 °C
3: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min
4: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
5: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C
6: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min
7: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature
8: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C
9: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h
10: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h
11: Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C
With
2,6-dimethylpyridine; dmap; Oxone; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; 1,1,1-trifluoro-2-propanone; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; edetate disodium; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; Monoperoxyphthalic acid, magnesium salt; triethylamine; trifluoroacetic acid; isobutene; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja971110h