Multi-step reaction with 8 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -20 - 0 °C / Inert atmosphere
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere
4.1: barium hydroxide octahydrate / tetrahydrofuran / 0.5 h / Inert atmosphere
4.2: Inert atmosphere
5.1: borane-dimethyl sulfide complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 1 h / -20 °C / Inert atmosphere
6.1: platinum(IV) oxide; hydrogen / ethyl acetate / 4 h / Inert atmosphere
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 0 °C / Inert atmosphere
8.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0 - 20 °C / Inert atmosphere
With
platinum(IV) oxide; borane-dimethyl sulfide complex; barium hydroxide octahydrate; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; diethylazodicarboxylate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;
4.1: Horner-Wadsworth-Emmons olefination / 8.1: Mitsunobu reaction;
DOI:10.1055/s-0030-1259967