Multi-step reaction with 11 steps
1.1: sodium tris(acetoxy)borohydride; acetic acid / 0.5 h / 0 °C / Inert atmosphere
2.1: pyridine / 0.25 h / 0 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere
4.1: lithium triethylborohydride / tetrahydrofuran / 24 h / 0 - 60 °C / Inert atmosphere
4.2: 1 h / 0 °C / Reflux
5.1: 1 h / Inert atmosphere; Reflux
6.1: potassium carbonate / 1,1,2,2-tetrachloroethane / 12 h / 150 °C / Inert atmosphere
7.1: potassium hydroxide / water; dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere
8.1: N-chloro-succinimide / chloroform / 0.5 h / -30 °C / Inert atmosphere
9.1: 15-crown-5; sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere
9.2: 11 h
10.1: lithium diisopropyl amide / tetrahydrofuran; hexane] / 1 h / -78 - 0 °C / Inert atmosphere
10.2: 2.5 h / 20 °C / Inert atmosphere
11.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / -78 °C
With
pyridine; N-chloro-succinimide; 15-crown-5; potassium tert-butylate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; chloroform; hexane]; water; dimethyl sulfoxide; 1,1,2,2-tetrachloroethane;
9.1: Grob fragmentation;
DOI:10.1021/jo1022487