Multi-step reaction with 9 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: 0.67 h / -78 - 20 °C / Inert atmosphere
2.1: (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trifluoroacetic acid / chloroform / 72 h / -30 °C / Inert atmosphere
3.1: toluene / 3 h / -78 °C / Inert atmosphere; Molecular sieve
3.2: 2 h / -78 - 20 °C / Inert atmosphere
4.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 0 - 40 °C / Inert atmosphere
5.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere
5.2: 2 h / 0 - 20 °C / Inert atmosphere
6.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 19 h / 0 - 20 °C / Inert atmosphere
7.1: ammonium molybdate tetrahydrate; dihydrogen peroxide / ethanol; water / 24 h / 20 °C / Inert atmosphere
8.1: lithium hexamethyldisilazane / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide / 0.17 h / -40 °C / Inert atmosphere
8.2: 24 h / -40 - 20 °C / Inert atmosphere
9.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere
With
pyridine; (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; oxalyl dichloride; ammonium molybdate tetrahydrate; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; pyridine hydrogenfluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
1.1: Swern oxidation / 1.2: Swern oxidation / 3.1: Roush crotylation / 6.1: Mitsunobu reaction / 8.2: Julia-Kocienski olefinaton;
DOI:10.1016/j.tet.2011.06.025