Multi-step reaction with 16 steps
1.1: ammonium nitrate / N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere
2.1: potassium tert-butylate / benzene / 0.5 h / 25 - 60 °C / Inert atmosphere
2.2: 0.25 h / 25 °C / Inert atmosphere
3.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide / 25 - 60 °C / Inert atmosphere
4.2: 15 h / 25 °C / Inert atmosphere
5.1: borane-THF / tetrahydrofuran / 72 h / 0 °C / Inert atmosphere
5.2: 0 - 25 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 130 °C / Microwave irradiation; Inert atmosphere
8.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere
9.1: sodium hydride / methanol / 0 - 25 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 4 h / 25 °C / Inert atmosphere
11.1: potassium tert-butylate / tert-butyl alcohol / 0.5 h / 25 °C / Inert atmosphere
12.1: ammonia; lithium / tetrahydrofuran; ethanol / -78 °C / Inert atmosphere
13.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
13.2: 0.5 h / 0 °C / Inert atmosphere
14.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 3 h / -78 °C / Inert atmosphere
15.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 60 °C / Inert atmosphere
15.2: 15 h / 20 °C / Inert atmosphere
16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 130 °C / Inert atmosphere; Microwave irradiation
With
ammonium nitrate; sodium tetrahydroborate; borane-THF; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; lithium; sodium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
5.1: Hydroboration reaction / 10.1: Michael addition / 11.1: Robinson cyclization;
DOI:10.1021/ol200966z