Multi-step reaction with 9 steps
1.1: lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 25 h / 20 °C / Inert atmosphere
2.2: 0.5 h / -78 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 45 h / 0 - 20 °C / Inert atmosphere
4.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 33 h / 0 - 20 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 6.5 h / -78 °C / Inert atmosphere
6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 38 h / 0 °C / Molecular sieve; Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
8.1: Jones reagent / acetone / 0.5 h / 0 °C / Inert atmosphere
9.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 5 h / 0 - 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; Jones reagent; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
8.1: Jones oxidation / 9.1: Pinnick oxidation;
DOI:10.1021/ol202306d