First synthesis of (±)-10β-hydroxy-13β-methylcyclohexa[a]quinolizidine. A convenient route to the ABC-part of 8-azasteroids

Abstract The first synthesis of racemic 10β-hydroxy-13β-methylcyclohexa[a]quinolizidine is reported. Original construction of AC -bicyclic system is achieved by lateral metallation of 2-ethylpyridine followed by a Robinson annelation, with the creation of a quaternary picolinic carbon center. Functionalization of the A -ring and construction of the B -ring by a stereocontrolled reduction of the pyridinium salt and final hydrogenations afford the ABC -part of an 8-azasteroid.