Multi-step reaction with 12 steps
1.1: magnesium; iodine / diethyl ether / 2 h / 20 °C
1.2: 2 h / 0 - 20 °C
2.1: propionic acid / benzene / 2 h / 150 °C
3.1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 19 h / 0 °C
4.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Reflux
5.1: toluene-4-sulfonic acid / toluene / 60 °C
6.1: 1H-imidazole; iodine / dichloromethane / 2.5 h / 0 - 20 °C
7.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C
7.2: -78 - 20 °C
8.1: sec.-butyllithium; (-)-sparteine / tert-butyl methyl ether; cyclohexane / 5 h / -78 °C
8.2: 21 h / -78 °C / Reflux
9.1: 1H-imidazole / dichloromethane / 20 °C
10.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -78 - 0 °C
10.2: 3 h / 20 °C
11.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 0 °C
12.1: acetyl chloride / methanol / 24 h / 20 °C
With
1H-imidazole; lithium aluminium tetrahydride; methanesulfonamide; AD-mix β; iodine; sec.-butyllithium; sodium hexamethyldisilazane; toluene-4-sulfonic acid; magnesium; propionic acid; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; (-)-sparteine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl methyl ether; cyclohexane; water; toluene; tert-butyl alcohol; benzene;
2.1: |Johnson-Claisen Rearrangement / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination;
DOI:10.1002/anie.201208403