Multi-step reaction with 12 steps
1: 97 percent / diethyl ether
2: 88 percent / diisobutylaluminium hydride / hexane; toluene / 0.25 h / 0 - 5 °C
3: 75 percent / barium manganate / CH2Cl2 / 4 h / Ambient temperature
4: 77 percent / (3aα,5aβ,6aβ,6bα)-6,6-dibromo-2-dimethylhexahydro-3aH-cyclopropa<1,3>benzodioxole / tetrahydrofuran; hexane / 3 h / -100 °C
5: 96 percent / H2 / 10percent palladium on charcoal / methanol / 1.5 h / 760 Torr
6: DMAP / pyridine / Ambient temperature
7: 90 percent / aq.HCl / tetrahydrofuran / 25 h / Ambient temperature
8: 1.) TFFA, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1.5 h, 2.) -60 deg C, 1.5 h
9: 75 percent / K2CO3 / acetone / 5 h / Ambient temperature
10: 85 percent / DBU / benzene / 1 h / Ambient temperature
11: 79 percent / K2CO3 / methanol / 2.5 h / Ambient temperature
12: Et3N / CH2Cl2 / 0.33 h / 0 - 5 °C
With
hydrogenchloride; dmap; barium manganate; (3aα,5aβ,6aβ,6bα)-6,6-dibromo-2-dimethylhexahydro-3aH-cyclopropa<1,3>benzodioxole; hydrogen; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; benzene;