Multi-step reaction with 9 steps
1: 1.) SOCl2 / 1.) reflux 2.) -78 deg C, THF
2: 90 percent / NH2OH.HCl / pyridine / 50 °C
3: 1.) Na 2.) HCl / 1.) i-PrOH, reflux 2.) Room temp.
4: 55 percent / mesitylmagnesium bromide / CH2Cl2 / Ambient temperature
5: 1.) N,N-diisopropylethylamine 2.) O3 / 1.) DMF, 0 deg C 2.) Me OH, -30 deg C, Me2S, R.T.
6: 85 percent / various solvent(s)
7: 72 percent / Ac2O / pyridine / Ambient temperature
8: HCl / methanol / 0 °C
9: 62 percent / 3,36,9,9-pentamethyl-2,10-diaza-bicyclo-4.4.o>-1-decene, O3 / methanol / -60 °C
With
hydrogenchloride; thionyl chloride; hydroxylamine hydrochloride; sodium; acetic anhydride; ozone; N-ethyl-N,N-diisopropylamine; 1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene; 2-mesitylmagnesium bromide;
hydrogenchloride;
In
pyridine; methanol; dichloromethane;
DOI:10.1016/S0040-4039(01)82981-6