Multi-step reaction with 9 steps
1.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 - 23 °C
2.1: 83 percent / DIBAL / CH2Cl2 / 2 h / -78 °C
3.1: N,N,N',N'-tetramethyl-1,2-ethanediamine; TMEDA / TiCl4 / CH2Cl2 / 0.33 h / 0 °C
3.2: 78 percent / CH2Cl2 / 1 h / 0 °C
4.1: 86 percent / N,N-diisopropylethylamine; Bu4NI / CH2Cl2 / 12 h / 0 - 23 °C
5.1: 80 percent / aq. NaBH4 / tetrahydrofuran / 12 h / 0 - 23 °C
6.1: 100 percent / pyridine / 5 h / 0 °C
7.1: 89 percent / NaI; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,2-dimethoxy-ethane / 3 h / Heating
8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 12 h / 0 - 23 °C
8.2: 84 percent / aq. NaOH / [PdCl2(1,1'-bis(diphenylphosphanyl)ferrocene)] / 4 h / 40 °C
9.1: 100 percent / TBAF / tetrahydrofuran / 48 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; sodium iodide;
titanium tetrachloride;
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
8.2: Suzuki cross-coupling;
DOI:10.1002/chem.200400617