Dipartimento di Scienze del Farmaco , Università del Piemonte Orientale , Largo Donegani 2 , 28100 Novara , Italy.
Dipartimento di Farmacia , Università di Napoli Federico II , Via Montesano 49 , 80131 Napoli , Italy.
Org Lett. 2019 Aug 2;21(15):6122-6125. doi: 10.1021/acs.orglett.9b02258. Epub 2019 Jul 24.
The thermal degradation of cannabichromene (CBC, ) is dominated by cationic reactions and not by the pericyclic rearrangements observed in model compounds. The rationalization of these differences inspired the development of a process that coupled, in an aromatization-driven single operational step, the condensation of citral and alkylresorciniols to homoprenylchromenes and their deconstructive annulation to benzo[]chromenes. This process was applied to a total synthesis of cannabinol (CBN, ) and to its molecular editing.
大麻色烯（CBC）的热降解主要由阳离子反应主导，而不是模型化合物中观察到的周环重排。这些差异的合理化激发了一种过程的发展，该过程在一个芳香化驱动的单一操作步骤中，将柠檬醛和烷基间苯二酚缩合为同丙烯基色烯，并将其解构性环合为苯并[]色烯。该过程被应用于大麻醇（CBN）的全合成及其分子编辑。
