Multi-step reaction with 16 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
1.3: -78 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 2.08 h / 0 - 25 °C / Inert atmosphere
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0.33 h / 20 - 25 °C / Inert atmosphere
4.1: quinoline; triethylsilane; 1-hexene / dichloromethane / 8 h / 20 - 25 °C / Inert atmosphere
5.1: diethyl ether / 2 h / -78 - 25 °C / Inert atmosphere
5.2: 1 h / Inert atmosphere; Reflux
6.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / -78 °C / Inert atmosphere
6.2: 1.5 h / -78 - -20 °C / Inert atmosphere
7.1: N-iodo-succinimide / 1,1,1,3',3',3'-hexafluoro-propanol / 0 °C / Inert atmosphere
8.1: water; potassium carbonate / methanol / 7.5 h / 20 - 25 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -10 °C / Inert atmosphere
9.2: 1.5 h / -10 - 25 °C / Inert atmosphere
9.3: 20 - 25 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / 20 - 25 °C / Inert atmosphere
11.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -78 °C / Inert atmosphere
11.2: -78 - 0 °C / Inert atmosphere
12.1: tert.-butyl lithium / diethyl ether; pentane / 1.17 h / -78 °C / Inert atmosphere
12.2: 1.03 h / -78 - 0 °C / Inert atmosphere
12.3: Inert atmosphere
13.1: pyridine; Dess-Martin periodane / dichloromethane / 0.25 h / 20 - 25 °C / Inert atmosphere
14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 20 - 25 °C / Inert atmosphere
14.2: 20 - 25 °C / Inert atmosphere
15.1: pyridinium p-toluenesulfonate / dichloromethane / 0.58 h / 0 - 25 °C / Inert atmosphere
16.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 24 h / 60 °C / Inert atmosphere
With
pyridine; quinoline; triethylsilane; N-iodo-succinimide; n-butyllithium; 1-hexene; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol; 1,2-dichloro-ethane; toluene; pentane;
1.2: Aldol addition / 5.1: Soderquist allylation / 11.1: Swern oxidation / 11.2: Swern oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1021/ol203342e