Multi-step reaction with 15 steps
1: diethyl ether / 0 °C
2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; caesium carbonate / tetrahydrofuran / Reflux
3: tetrabutyl ammonium fluoride / tetrahydrofuran
4: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C
5: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
6: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C
7: sodium hydride / tetrahydrofuran / 0 °C
8: 2-hydroxynitrobenzene / 144 h / 130 °C / Inert atmosphere
9: sodium hydroxide / methanol; water / 80 °C
10: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
11: Dess-Martin periodane / dichloromethane
12: boron trifluoride diethyl etherate / dichloromethane / 3 h / -10 °C
13: diphenylsilyl chloride; indium(III) chloride / 1,2-dichloro-ethane / 21 h / Reflux
14: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C
15: (1S)-10-camphorsulfonic acid / tetrahydrofuran / Reflux
With
indium(III) chloride; lithium aluminium tetrahydride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; tributylphosphine; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; diphenylsilyl chloride; tetrabutyl ammonium fluoride; sodium hydride; caesium carbonate; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2-hydroxynitrobenzene; sodium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
2: |Suzuki Coupling / 4: |Mitsunobu Displacement / 8: |Claisen Rearrangement;
DOI:10.1055/s-0032-1318114