Multi-step reaction with 9 steps
1.1: 95 percent / K2OsO2(OH)4; K2CO3; DHQ2PHAL / K3Fe(CN)6 / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
2.1: 90 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: 84 percent / BF3*Et2O / tetrahydrofuran; hexane / 1 h / -78 °C
4.1: 100 percent / KH / dimethylformamide / 0.75 h / 0 °C
5.1: 86 percent / N-bromosuccinimide / dimethylformamide / 1 h / 0 °C
6.1: n-BuLi / tetrahydrofuran / 0.42 h / -78 °C
6.2: 88 percent / tetrahydrofuran / 0.42 h / -78 °C
7.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C
7.2: 96 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 0.5 h / 0 °C
8.1: 75 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / 20 °C
9.1: 89 percent / HF*pyridine / tetrahydrofuran / 1 h / 0 °C
With
dmap; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; potassium dioxotetrahydroxoosmate(VI); di-isopropyl azodicarboxylate; potassium hydride; potassium carbonate; pyridine hydrogenfluoride; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine;
potassium hexacyanoferrate(III);
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
1.1: Sharpless asymmetric dihydroxylation / 8.1: Mitsunobu coupling;
DOI:10.1016/j.tet.2007.04.031