Multi-step reaction with 13 steps
1.1: hydrogen fluoride / pyridine; tetrahydrofuran / 6 h / 0 - 20 °C
2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 5 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C
3.2: 0.25 h / 0 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C
5.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.33 h / -78 °C
6.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 6 h / 20 °C
7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -28 - 0 °C
7.2: 1.5 h / -78 - 20 °C
8.1: hydrogen / methanol / 18 h / 20 °C
9.1: hydrogenchloride / dichloromethane; water
10.1: N-ethyl-N,N-diisopropylamine; oxygen; rose bengal / methanol / 1 h / -78 °C / Irradiation
11.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 °C
12.1: hydrogenchloride / methanol / 17 h / 20 °C / pH 2
13.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen fluoride; hydrogen; oxygen; rose bengal; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water;
3.1: |Wittig Olefination / 3.2: |Wittig Olefination / 11.1: |Luche Cerium Reduction;
DOI:10.1055/s-0033-1338934