Multi-step reaction with 18 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
1.3: 2 h / -78 - 0 °C / Inert atmosphere
2.1: dichloromethane / 1.5 h / 25 °C / Inert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 14 h / 0 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.2: 16 h / 25 °C / Inert atmosphere
5.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 1 h / -25 °C / Inert atmosphere; Molecular sieve
5.2: 17 h / -20 °C / Inert atmosphere; Molecular sieve
6.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere
7.1: dichloromethane / 14 h / 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
9.1: pyridinium p-toluenesulfonate / dichloromethane / 25 - 40 °C / Inert atmosphere
10.1: lanthanum(lll) triflate / toluene / 6 h / 25 °C / Inert atmosphere
11.1: sodium tetrahydroborate; nickel (II) chloride hexahydrate / ethanol / 0 °C / Inert atmosphere
12.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.5 h / 25 °C / Inert atmosphere
13.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere
14.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / 0 °C / Inert atmosphere
14.2: 0.33 h / 0 °C / Inert atmosphere
15.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 3 h / 0 °C / Inert atmosphere
16.1: dmap; 2-methyl-6-nitrobenzoic anhydride; triethylamine / toluene / 0.33 h / 25 °C / Inert atmosphere; Molecular sieve
16.2: 13 h / 25 °C / Inert atmosphere; Molecular sieve
17.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 0.67 h / 0 °C / Inert atmosphere
18.1: N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride / tetrahydrofuran; dichloromethane / 0 - 25 °C / Inert atmosphere
18.2: 0.67 h / 25 °C / Inert atmosphere
With
2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; nickel (II) chloride hexahydrate; diethyl (2S,3S)-tartrate; N,N,N,N,-tetramethylethylenediamine; 2-methyl-6-nitrobenzoic anhydride; p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lanthanum(lll) triflate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
1.1: Swern oxidation / 1.2: Swern oxidation / 1.3: Swern oxidation / 2.1: Wittig reaction / 5.1: Sharpless epoxidation / 5.2: Sharpless epoxidation / 6.1: Parikh-Doering oxidation / 7.1: Wittig reaction / 13.1: Parikh-Doering oxidation / 14.1: Wittig reaction / 14.2: Wittig reaction;
DOI:10.1021/ja109533y