Multi-step reaction with 9 steps
1.1: borane-dimethyl sulfide complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane / 3 h / 0 °C
2.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
3.1: L-diisopinocampheylborane / tetrahydrofuran / 5 h / 0 - 20 °C
3.2: 1.75 h / 0 - 12 °C
4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
5.1: triethylamine / dichloromethane / 1 h / 0 - 5 °C
6.1: 3-chloro-benzenecarboperoxoic acid; disodium hydrogenphosphate / dichloromethane / 2.5 h / -25 °C
6.2: -25 - 20 °C
7.1: titanium tetrachloride / tetrahydrofuran / 3.5 h / -40 - 20 °C
8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / -20 °C
9.1: toluene-4-sulfonic acid; methanol / 4 h / 0 - 20 °C
With
1H-imidazole; methanol; disodium hydrogenphosphate; borane-dimethyl sulfide complex; titanium tetrachloride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; L-diisopinocampheylborane; diethylazodicarboxylate;
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane;
8.1: Mitsunobu reaction;