Multi-step reaction with 16 steps
1.1: 71 percent / DIBALH / CH2Cl2 / 0.5 h / -78 - 0 °C
2.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.25 h / -78 - 0 °C
3.1: tetrahydrofuran / 0.17 h / -78 °C
4.1: 90 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.25 h / -78 - 0 °C
5.1: 71 percent / Zn(BH4)2 / diethyl ether / 0.33 h / -30 °C
6.1: VO(acac)2; TBHP / CH2Cl2 / 3.5 h / 0 °C
7.1: 83 percent / NaH; Bu4NI / tetrahydrofuran / 2 h / 23 °C
8.1: DDQ / CH2Cl2 / 3.5 h / 26 °C / pH 7
9.1: 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
10.1: t-BuLi; Bu2Mg / tetrahydrofuran / 0.5 h / -20 °C
10.2: 72 percent / tetrahydrofuran / 1 h / 23 °C
11.1: 87 percent / 2,6-lutidine / dimethylformamide / 1.17 h / 0 °C
12.1: 72 percent / Hg(ClO4)2; 2,6-di-tert-butylpyridine / tetrahydrofuran; H2O / 0.25 h / 25 °C
13.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C
13.2: 97 percent / tetrahydrofuran / 2 h / -78 °C
14.1: 100 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
15.1: NaH / benzene; tetrahydrofuran / 0.08 h / 0 °C
15.2: 85 percent / benzene; tetrahydrofuran / 8 h / -78 °C
16.1: 98 percent / NaBH4; CeCl3*H2O / ethanol / 3 h / -20 °C
With
2,6-dimethylpyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; 2,6-di-tert-butyl-pyridine; cerium(III) chloride; zinc(II) tetrahydroborate; mercury(II) perchlorate; oxalyl dichloride; bis(acetylacetonate)oxovanadium; dibutylmagnesium; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
2.1: Swern oxidation / 4.1: Swern oxidation / 15.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2007.04.136