Multi-step reaction with 8 steps
1: 1.) DIBAL, 2.) MeOH / 1.) CH2Cl2, hexane, -78 deg C, 4 h, 2.) CH2Cl2, hexane, RT, 30 min
2: 1.) NaH / 1.) THF, DMSO, RT, 1 h, 2.) THF, DMSO, RT, 2 h
3: 81 percent / phosphate buffer (pH 7), DDQ / CH2Cl2 / 3 h / Ambient temperature
4: DMSO, oxalyl chloride / CH2Cl2 / 0.75 h / -78 °C
5: tetrahydrofuran / 3 h / -78 - 20 °C
6: 55 percent / AD-mix-α, NaHCO3 / 2-methyl-propan-2-ol / 24 h / 4 °C
7: 58 percent / pyridine, 4-dimethylaminopyridine / 96 h / Ambient temperature
8: H2 / Pd(OH)2/C / ethanol / 5 h / Ambient temperature
With
pyridine; methanol; dmap; AD-mix-α; phosphate buffer; oxalyl dichloride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium dihydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol;
DOI:10.1248/cpb.44.1819