Multi-step reaction with 13 steps
1: 98 percent / sodium borohydride / ethanol / 0 °C
2: 97 percent / i-Pr2NEt, 4-DMAP / CH2Cl2 / Ambient temperature
3: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -78 deg C; 2.) CH2Cl2, r.t.
4: Ph3P, i-PrO2CN=NCO2i-Pr / tetrahydrofuran / Ambient temperature
5: n-Bu4NF / tetrahydrofuran / Ambient temperature
6: CH2Cl2 / -78 - 20 °C / Swern oxidn.
7: NaH / 1,2-dimethoxy-ethane / Ambient temperature
8: 95 percent / H2 / Pd/C / ethanol / Ambient temperature
9: 85 percent / HCl, EtOH / 60 °C
10: 91 percent / CH2Cl2 / -78 - 20 °C / Swern oxidn.
11: 79 percent / lithium hexamethyldisilazide, HMPA / tetrahydrofuran / -78 °C
12: pyridine, 4-DMAP / Ambient temperature
13: DBU / 110 °C
With
pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; ethanol; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane;