Multi-step reaction with 12 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
10.1: zirconium(IV) chloride / isopropyl alcohol / 9 h / Reflux; Inert atmosphere
11.1: tetrabutyl ammonium fluoride; triethylamine; copper(ll) bromide / dichloromethane / 2 h / 0 - 20 °C / Molecular sieve; Darkness; Inert atmosphere
12.1: 2,6-dimethylpyridine / 1,2-dichloro-ethane / 2 h / Reflux; 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; zirconium(IV) chloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine; N-ethyl-N,N-diisopropylamine; copper(ll) bromide; lithium hydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol;
8.1: Jones oxidation / 9.1: Pinnick oxidation;
DOI:10.1021/ol202306d