Multi-step reaction with 21 steps
1: dihydrogen peroxide; sodium hydroxide
2: cerium(III) chloride heptahydrate; sodium hypochlorite solution / dichloromethane; water / 0 °C
3: N-ethylmorpholine N-oxide; lithium iodide / N,N-dimethyl-formamide / 30 h / 55 °C
4: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 0 °C
5: 0 °C
6: pyridinium p-toluenesulfonate / acetone / 45 °C
7: dichloromethane / 36 h / 28 °C / Inert atmosphere
8: triethylamine / dichloromethane / -78 °C
9: 2,6-di-tert-butyl-4-methyl-phenol / toluene; methyloxirane / 96 h / 140 °C / Inert atmosphere
10: diethylzinc / hexane; toluene / 4 h / 0 °C
11: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / -30 - 20 °C
12: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 0 °C
13: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; diethylaluminium chloride / hexane; toluene / 1.33 h / 0 °C
14: Grubbs catalyst first generation; p-benzoquinone / dichloromethane / 1 h / Reflux
15: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 20 °C / Inert atmosphere
16: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Molecular sieve
17: fluorosilicic acid / water; acetonitrile / 18 h / 0 - 4 °C
18: sodium hydroxide / 1,4-dioxane; water / 6 h / 90 °C / Inert atmosphere
19: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.83 h / -78 - 20 °C
20: manganese(IV) oxide / chloroform / 20 °C
21: dmap / dichloromethane
With
2,2,6,6-tetramethyl-piperidine; Grubbs catalyst first generation; dmap; manganese(IV) oxide; sodium chlorite; sodium tetrahydroborate; n-butyllithium; N-ethylmorpholine N-oxide; sodium hypochlorite solution; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; cerium(III) chloride heptahydrate; 2,6-di-tert-butyl-4-methyl-phenol; fluorosilicic acid; dihydrogen peroxide; diethylzinc; diethylaluminium chloride; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; sodium hydroxide; lithium iodide;
In
1,4-dioxane; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; methyloxirane; mineral oil; tert-butyl alcohol; benzene;
DOI:10.1021/jo3008034