Multi-step reaction with 14 steps
1: 65 percent / LDA / tetrahydrofuran / -78 °C
2: NaBH4 / methanol; tetrahydrofuran / 0.5 h / Ambient temperature
3: 100 percent / Et3N / CH2Cl2 / 0.67 h / 0 °C
4: 96 percent / 1.) BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) room temp., 2 d
5: 5 molpercent H2SO4 / dioxane / 0.33 h / Ambient temperature
6: DMAP / pyridine / 24 h / 40 °C
7: 2percent HCl / methanol / 0.5 h / Ambient temperature
8: H2 / Pd-C / acetic acid; ethanol / 2 h / Ambient temperature
9: air, 10 molpercent Cu(OAc)2 / acetic acid; H2O; ethanol / 0.67 h / Ambient temperature
10: 87 percent / 3.63M t-BuOOH, 40 molpercent VO(acac)2 / CH2Cl2; toluene / 0.33 h / 0 °C
11: Et3N / CH2Cl2 / 0.25 h / 0 °C
12: DBU / toluene / 1.67 h / 40 °C
13: K2CO3 / methanol / 1 h / Ambient temperature
14: 98 percent / DMSO, DCC, pyridin, TFA / diethyl ether / 1.5 h / Ambient temperature
With
pyridine; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; copper diacetate; bis(acetylacetonate)oxovanadium; air; sulfuric acid; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide;
dmap; palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; acetic acid; toluene;
DOI:10.1016/S0040-4039(00)61737-9