Collect. Czech. Chem. Commun. 1988, 53, 3184-3192

Synthesis of fagaronine

Jan Šmidrkal

Research Institute of Fat Industry, 269 01 Rakovnik


Alkaloids fagaronine (I), dihydrofagaronine (XXV) and oxyfagaronine (XXVI) were synthesized from 2,3-dihydroxynaphthalene (II) and 2-bromo-4,5-dimethoxybenzaldehyde (XI), the key synthetic steps being the preparation of 2-hydroxy-3-methoxy-5-nitronaphthalene (VI) by partial methylation of 2,3-dihydroxy-5-nitronaphthalene (V) and formation of benzo[c]phenanthridone XXI by photocyclization of amide XVI.