Multi-step reaction with 9 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C
1.2: 1 h / Reflux
2.1: rhodium(II) acetate dimer / 1,2-dichloro-ethane / 1.83 h / Reflux
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.33 h / -78 - 0 °C
3.2: 1.67 h / -78 - 20 °C
4.1: sodium hydrogencarbonate; dihydrogen peroxide / tetrahydrofuran; water / 72 h / 20 °C
5.1: [Cu{(S,S)-t-Bu-box}(tfe)2](SbF6)2 / dichloromethane; 1,2-dichloro-ethane / 18 h / 20 °C
6.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / dichloromethane; tetrahydrofuran / 0.33 h / -82 °C
6.2: 0.58 h / -82 - -72 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C
8.2: 1 h / 20 °C
8.3: 2 h / -46 - -4 °C
9.1: dmap; dicyclohexyl-carbodiimide / ethylene dibromide / 16 h / 0 - 20 °C
With
dmap; lithium aluminium tetrahydride; rhodium(II) acetate dimer; [Cu{(S,S)-t-Bu-box}(tfe)2](SbF6)2; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; ethylene dibromide; mineral oil;
3.2: |Horner-Wadsworth-Emmons Olefination / 5.1: |Claisen Rearrangement / 9.1: |Steglich Esterification;
DOI:10.1021/jo5001466