Multi-step reaction with 22 steps
1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 25 - 60 °C / Inert atmosphere
2.2: 15 h / 25 °C / Inert atmosphere
3.1: borane-THF / tetrahydrofuran / 72 h / 0 °C / Inert atmosphere
3.2: 0 - 25 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 130 °C / Microwave irradiation; Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere
7.1: sodium hydride / methanol / 0 - 25 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 4 h / 25 °C / Inert atmosphere
9.1: potassium tert-butylate / tert-butyl alcohol / 0.5 h / 25 °C / Inert atmosphere
10.1: ammonia; lithium / tetrahydrofuran; ethanol / -78 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
11.2: 0.5 h / 0 °C / Inert atmosphere
12.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 3 h / -78 °C / Inert atmosphere
13.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 60 °C / Inert atmosphere
13.2: 15 h / 20 °C / Inert atmosphere
14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 130 °C / Inert atmosphere; Microwave irradiation
15.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere
16.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere
17.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
17.2: 1 h / -78 °C / Inert atmosphere
18.1: formic acid; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine / N,N-dimethyl-formamide / 1 h / 75 °C / Inert atmosphere
19.1: borane-THF / tetrahydrofuran / 15 h / Inert atmosphere; Reflux
19.2: 0 - 20 °C / Inert atmosphere
19.3: 0 - 20 °C / Inert atmosphere
20.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
21.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium tert-butoxide / tetrahydrofuran / 1 h / 70 °C / Inert atmosphere
22.1: tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; formic acid; borane-THF; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; palladium diacetate; sodium hexamethyldisilazane; lithium; sodium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium tert-butoxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
3.1: Hydroboration reaction / 8.1: Michael addition / 9.1: Robinson cyclization / 19.1: Hydroboration reaction;
DOI:10.1021/ol200966z