Multi-step reaction with 11 steps
1.1: NMO; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 19 h
2.1: sodium periodate / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1.5 h
3.1: 9.95 g / 2-methyl-2-butene; NaH2PO4; sodium chlorite / 2-methyl-propan-2-ol; H2O
4.1: triethylamine / tetrahydrofuran / -78 - 20 °C
5.1: 15.5 g / n-BuLi / tetrahydrofuran / -78 - 0 °C
6.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C
6.2: 76 percent / Davis reagent / tetrahydrofuran / 0.17 h
7.1: 67 percent / diisopropylethylamine / CH2Cl2 / 0 °C
8.1: 81 percent / LiBH4 / tetrahydrofuran; H2O / 2 h / 0 °C
9.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
10.1: Mg; iodine / diethyl ether / 1 h
10.2: 85 percent / diethyl ether / -78 - 0 °C
11.1: 86 percent / pyridine; Dess-Martin periodinane / CH2Cl2
With
pyridine; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; 2-methyl-but-2-ene; oxalyl dichloride; iodine; sodium hexamethyldisilazane; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;
9.1: Swern oxidation;
DOI:10.1016/j.tet.2006.03.066