New hexahydro-dibenz[d,f]azecines, 11 and 12, were synthesized from the homoerythrinan-enone 3. Their 6-oxo derivatives were shown to exist in two conformations in solution due to the rotational isomerism of the ten-membered lactam group. An example of remarkably large separation of two methylenedioxy protons in the proton nuclear magnetic resonance spectrum due to their non-equivalence is also presented.
- f]-azecine tetrahydro-dibenz[d
- f]azecin-6(5h)-one conformational isomer rotational isomerism ten-membered lactam methylenedioxy group ]H-NMR
- f]azecine alkaloid homoerythrinan-enone hexahydro-dibenz[d
ASJC Scopus subject areas
- Drug Discovery