A Synthesis of (±)-Dihydrodeoxyepiallocernuine by Application of a Facile Hofmann-Loeffler Type of Photocyclization

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Pelletierine which was established to be a precursor in the biosynthesis of cernuine (1), was converted into the quinolizidine (22), whose N-chloro derivative (27) was irradiated with 300 W high pressure mercury lamp in ether in the absence of any strong acid to readily afford the entitled compound (3) as the free base with no base treatment. The present photocyclization is thus different from the known Hofmann-Loeffler reaction in several respects, which are demonstrated for discussion.