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. 2022 Aug 6;12(8):1084. doi: 10.3390/biom12081084

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© 2022 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

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Scheme 2 — (A) Iodine-promoted cyclization of Δ⁹-THC (1) to CBN (7); (B) iodine-promoted prenylchromene-benzochromane rearrangement of CBC (4) to CBN (7). R = n-pentyl. The two terminal arrows indicate additional dehydrogenation, for which 1,4-addition of iodine followed by two-fold dehydrohalogenation seems plausible [97].