Multi-step reaction with 16 steps
1: triethylamine; iodine / tetrahydrofuran / 3 h / -40 °C / Inert atmosphere
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 100 °C / Inert atmosphere
3: hydrogenchloride / methanol / 3 h / 20 °C / Inert atmosphere
4: tert.-butyl lithium / diethyl ether / -78 °C / Inert atmosphere
5: pyridinium chlorochromate / dichloromethane / Inert atmosphere
6: lithium triethylborohydride / tetrahydrofuran / Inert atmosphere
7: triethylamine / dichloromethane / Inert atmosphere
8: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere
9: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / Inert atmosphere; Molecular sieve
10: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere
11: phthalic acid dimethyl ester; sodium hydrogencarbonate / dichloromethane / Inert atmosphere
12: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 24 h / Inert atmosphere; Reflux
13: tris(triphenylphosphine)rhodium(l) chloride; hydrogen / benzene / 3 h / 70 °C / Inert atmosphere
14: pyridine hydrogenfluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
15: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 0.5 h / 0 °C / Inert atmosphere
16: triethylamine; dmap / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
With
hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; tetrapropylammonium perruthennate; tris(triphenylphosphine)rhodium(l) chloride; cerium(III) chloride heptahydrate; phthalic acid dimethyl ester; 2,6-di-tert-butyl-4-methyl-phenol; hydrogen; iodine; tert.-butyl lithium; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene;
DOI:10.1021/jo4006156