Multi-step reaction with 18 steps
1.1: 100 percent / TBAI; NaH / tetrahydrofuran / 16 h / 0 - 25 °C
2.1: 88 percent / diisobutyl aluminium hydride / CH2Cl2; hexane / 2 h / -78 °C
3.1: TBAI; NaH / tetrahydrofuran / 21 h / 0 - 25 °C
4.1: TBAF / tetrahydrofuran / 2 h / 25 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 0 - 23 °C
6.1: NHMDS / tetrahydrofuran / 0.5 h / 0 °C
6.2: tetrahydrofuran / 17 h / -78 - 23 °C
7.1: 99 percent / Hg(OAc)2; TBAI / tetrahydrofuran; H2O / 3 h / 24 °C
8.1: 40 percent / CrCl2; NiCl2 / dimethylsulfoxide / 25 h / 25 °C
9.1: VO(acac)2; TBHP / toluene / 2.5 h / 0 °C
9.2: 91 percent / dimethylsulfide / toluene / 0.5 h / 24 °C
10.1: 100 percent / 2,6-lutidine / tetrahydrofuran / 0.17 h / 0 - 25 °C
11.1: 97 percent / DDQ; pH 7 buffer / CH2Cl2 / 0.83 h / 0 °C / pH 7
12.1: CSA / CH2Cl2 / 0.42 h / 0 °C
12.2: 80 percent / triethylamine / CH2Cl2 / 0.5 h / 0 - 25 °C
13.1: 61 percent / (COCl)2; triethylamine; DMSO / CH2Cl2 / 1.25 h / -78 - 0 °C
14.1: 71 percent / HF*Py; pyridine / tetrahydrofuran / 144 h / 25 °C
15.1: 27 percent / NaBH4 / methanol / 0.25 h / 0 °C
16.1: PPTS / benzene / 3 h / 80 °C
17.1: DIBAL / CH2Cl2; hexane / 2 h / -20 °C
18.1: 71 percent / TBAI; NaH / tetrahydrofuran / 120 h / 0 - 25 °C
With
pyridine; 2,6-dimethylpyridine; chromium dichloride; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; bis(acetylacetonate)oxovanadium; pH 7 buffer; camphor-10-sulfonic acid; mercury(II) diacetate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; benzene;
6.2: Wittig reaction / 8.1: Nozaki-Hiyama-Kishi reaction / 13.1: Swern oxidation;
DOI:10.1016/j.tet.2006.05.014