Multi-step reaction with 9 steps
1.1: ethanol / 20 °C / Inert atmosphere
1.2: 2 h / Reflux; Inert atmosphere
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
3.1: pyridinium chlorochromate / dichloromethane / 6 h / 20 °C / Inert atmosphere; Molecular sieve
4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
7.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
8.1: hydrazine hydrate / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere
9.1: N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
With
lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; sodium hydride; hydrazine hydrate; triphenylphosphine; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
4.1: Horner-Wadsworth-Emmons olefination / 7.1: Mitsunobu reaction;
DOI:10.1021/jm2001376