Multi-step reaction with 13 steps
1.1: 8.8 g / t-BuOK / tetrahydrofuran / 6 h / 20 °C
2.1: lithium borohydride / tetrahydrofuran / 0.5 h / 20 °C
2.2: tetrahydrofuran; methanol / 24 h / 20 °C
3.1: 3.9 g / NMO; TPAP / CH2Cl2 / 18 h / 20 °C
4.1: tetrahydrofuran / 11.5 h / -78 - 20 °C
4.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C
5.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C
6.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C
7.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C
8.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C
9.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C
10.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
11.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C
12.1: K2CO3; MeOH / 15 h / 20 °C
13.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C
With
pyridine; 1.3-propanedithiol; hydrogenchloride; methanol; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; potassium tert-butylate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; dichloromethane; 2,2,2-trifluoroethanol; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ol0706051