From cannabinol (CBN) to cannabiphenanthrene (CNP) via a photochemical cascade reaction. A steady-state and time-resolved spectroscopic investigation☉

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The photochemical conversion of phytocannabinoid Cannabinol (CBN) into Cannabiphenanthrene (CNP) was investigated in detail via a combined steady-state/time-resolved approach and supplemented by computational simulations. The elucidated mechanism describes a two-photon cascade reaction, where CBN is initially converted to cannabinodiol (CBND) via a photoinduced C–O cleavage, which in turn undergoes a 6π−electrocyclization to form the corresponding cannabiphenanthrene.