Multi-step reaction with 28 steps
1.1: diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: 20 % Pd(OH)2/C; hydrogen / ethanol; ethyl acetate / 18 h / 25 °C
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 18 h / 25 °C / Inert atmosphere
4.1: dichloromethane / 4 h / 25 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C / Inert atmosphere
7.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.33 h / -20 °C / Molecular sieve; Inert atmosphere
7.2: 1 h / -20 °C / Inert atmosphere
8.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 9 h / 0 - 25 °C / Inert atmosphere
9.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
9.2: 1 h / -78 - 0 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
11.1: camphor-10-sulfonic acid / dichloromethane / 0.5 h / 25 °C / Inert atmosphere
12.1: 1H-imidazole / dichloromethane / 0 - 25 °C / Inert atmosphere
13.1: borane-THF / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
13.2: 1 h / 0 °C
14.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 0 - 25 °C / Molecular sieve; Inert atmosphere
15.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C / Inert atmosphere
16.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 12 h / 0 - 25 °C / Molecular sieve; Inert atmosphere
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
18.1: 4-methyl-morpholine / dichloromethane / 23 h / 25 °C / Inert atmosphere
19.1: methanol; samarium diiodide / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
20.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
21.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere
22.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / 0 °C / Inert atmosphere
22.2: 1 h / 0 °C / Inert atmosphere
23.1: diisobutylaluminium hydride / dichloromethane / 0.67 h / -78 °C / Inert atmosphere
24.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve; Inert atmosphere
24.2: 1 h / -20 °C / Inert atmosphere
25.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 1 h / 25 °C / Inert atmosphere
26.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
26.2: -78 - 0 °C / Inert atmosphere
27.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
28.1: camphor-10-sulfonic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere
With
4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; methanol; samarium diiodide; tetrapropylammonium perruthennate; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; 20 % Pd(OH)2/C; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene;
1.1: Grignard reaction / 7.1: Sharpless epoxidation / 7.2: Sharpless epoxidation / 9.1: Whiting reaction / 9.2: Whiting reaction / 22.1: Horner-Wadsworth-Emmons olefination / 22.2: Horner-Wadsworth-Emmons olefination / 24.1: Sharpless epoxidation / 24.2: Sharpless epoxidation;
DOI:10.1021/ja109531d