Multi-step reaction with 12 steps
1.1: 98 percent / aq. HCl / tetrahydrofuran / 21 h / 25 °C
2.1: 2,6-lutidine / CH2Cl2 / 0.25 h / -78 °C
3.1: 17.5 mg / 2,6-lutidine / CH2Cl2 / 1 h / -78 - 0 °C
4.1: BuLi / tetrahydrofuran / 0.17 h / -78 °C
4.2: 99 percent / tetrahydrofuran / 3 h / -78 - 24 °C
5.1: Cp2ZrCl2; DIBAL / tetrahydrofuran; hexane / 0.5 h / 55 °C
5.2: 86 percent / I2 / tetrahydrofuran; hexane / 0.25 h / 0 °C
6.1: 40 percent / CrCl2; NiCl2 / dimethylsulfoxide / 25 h / 25 °C
7.1: VO(acac)2; TBHP / toluene / 2.5 h / 0 °C
7.2: 91 percent / dimethylsulfide / toluene / 0.5 h / 24 °C
8.1: 100 percent / 2,6-lutidine / tetrahydrofuran / 0.17 h / 0 - 25 °C
9.1: 97 percent / DDQ; pH 7 buffer / CH2Cl2 / 0.83 h / 0 °C / pH 7
10.1: CSA / CH2Cl2 / 0.42 h / 0 °C
10.2: 80 percent / triethylamine / CH2Cl2 / 0.5 h / 0 - 25 °C
11.1: 61 percent / (COCl)2; triethylamine; DMSO / CH2Cl2 / 1.25 h / -78 - 0 °C
12.1: 71 percent / HF*Py; pyridine / tetrahydrofuran / 144 h / 25 °C
With
pyridine; 2,6-dimethylpyridine; chromium dichloride; hydrogenchloride; tert.-butylhydroperoxide; n-butyllithium; zirconocene dichloride; oxalyl dichloride; bis(acetylacetonate)oxovanadium; pH 7 buffer; camphor-10-sulfonic acid; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene;
6.1: Nozaki-Hiyama-Kishi reaction / 11.1: Swern oxidation;
DOI:10.1016/j.tet.2006.05.014
