Multi-step reaction with 23 steps
1.1: dichloromethane / 1.5 h / 25 °C / Inert atmosphere
2.1: 2,6-dimethylpyridine / dichloromethane / 14 h / 0 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere
3.2: 16 h / 25 °C / Inert atmosphere
4.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 1 h / -25 °C / Inert atmosphere; Molecular sieve
4.2: 17 h / -20 °C / Inert atmosphere; Molecular sieve
5.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere
6.1: dichloromethane / 14 h / 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
8.1: pyridinium p-toluenesulfonate / dichloromethane / 25 - 40 °C / Inert atmosphere
9.1: lanthanum(lll) triflate / toluene / 6 h / 25 °C / Inert atmosphere
10.1: sodium tetrahydroborate; nickel (II) chloride hexahydrate / ethanol / 0 °C / Inert atmosphere
11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.5 h / 25 °C / Inert atmosphere
12.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 25 °C / Inert atmosphere
13.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / 0 °C / Inert atmosphere
13.2: 0.33 h / 0 °C / Inert atmosphere
14.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 3 h / 0 °C / Inert atmosphere
15.1: dmap; 2-methyl-6-nitrobenzoic anhydride; triethylamine / toluene / 0.33 h / 25 °C / Inert atmosphere; Molecular sieve
15.2: 13 h / 25 °C / Inert atmosphere; Molecular sieve
16.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 0.67 h / 0 °C / Inert atmosphere
17.1: N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride / tetrahydrofuran; dichloromethane / 0 - 25 °C / Inert atmosphere
17.2: 0.67 h / 25 °C / Inert atmosphere
18.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
19.1: bis(cyclohexanyl)borane / tetrahydrofuran / 6 h / 25 °C / Inert atmosphere
19.2: 20 h / 0 °C / Inert atmosphere
20.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 25 °C / Inert atmosphere
21.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 0.5 h / 0 °C / Inert atmosphere
22.1: zinc trifluoromethanesulfonate / dichloromethane / 16 h / 25 °C / Inert atmosphere
23.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -78 - 30 °C / Inert atmosphere
23.2: -78 - 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; nickel (II) chloride hexahydrate; diethyl (2S,3S)-tartrate; N,N,N,N,-tetramethylethylenediamine; bis(cyclohexanyl)borane; 2-methyl-6-nitrobenzoic anhydride; p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lanthanum(lll) triflate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
1.1: Wittig reaction / 4.1: Sharpless epoxidation / 4.2: Sharpless epoxidation / 5.1: Parikh-Doering oxidation / 6.1: Wittig reaction / 12.1: Parikh-Doering oxidation / 13.1: Wittig reaction / 13.2: Wittig reaction / 19.1: Hydroboration reaction;
DOI:10.1021/ja109533y