Multi-step reaction with 16 steps
1.1: O3 / CH2Cl2; methanol / -78 °C
1.2: 97 percent / NaBH4 / CH2Cl2; methanol / 1.5 h / -78 - 23 °C
2.1: TEMPO; aq. KBr; NaOCl / NaHCO3 / CH2Cl2 / 0.33 h / 0 °C
3.1: 18-crown-6; TMSCN / CH2Cl2 / 1 h / 23 °C
3.2: 1.14 g / pyridinium p-toluenesulfonate / CH2Cl2; methanol / 5 h / 23 °C
4.1: 88 percent / pyridinium p-toluenesulfonate / acetone / 19 h / 68 °C
5.1: 92 percent / LDA; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; hexane / 0.5 h / -40 °C
6.1: Dowex 50X2-100 ion-exchange resin; H2O / methanol / 12 h / 23 °C
7.1: 0.74 g / Et3N / methanol / 23 °C
8.1: 89 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 23 °C
9.1: 97 percent / imidazole; DMAP / dimethylformamide / 13 h / 23 °C
10.1: 93 percent / Li; NH3 / tetrahydrofuran / 0.2 h / -78 °C
11.1: 92 percent / I2; PPh3; imidazole / benzene / 0.17 h / 23 °C
12.1: 93 percent / LDA; N,N'-dimethyl-N,N'-propyleneurea / tetrahydrofuran; hexane / 0.25 h / -40 °C
13.1: 91 percent / NMO; OsO4 / 2-methyl-propan-2-ol; H2O / 12.75 h / 23 °C
14.1: 94 percent / Pb(OAc)4; Na2CO3 / CH2Cl2 / 0.75 h / -10 - 23 °C
15.1: 90 percent / n-BuLi; DMPU / tetrahydrofuran / 0.25 h / -78 °C
With
1H-imidazole; lead(IV) acetate; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 18-crown-6 ether; trimethylsilyl cyanide; Dowex 50X2-100 ion-exchange resin; ammonia; water; iodine; pyridinium p-toluenesulfonate; lithium; sodium carbonate; ozone; triethylamine; triphenylphosphine; potassium bromide; lithium diisopropyl amide;
sodium hydrogencarbonate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1002/anie.200453697