Domino reactions, those that include at least two consecutive reactions such that each subsequent reaction occurs because of the previous step, are an efficient way to synthesize complex molecules from simple starting materials. The purpose of this project is to develop a domino reaction that includes a carbonyl-ene/elimination/Diels-Alder reaction to produce cannabinoid and anthracene derivatives. These structures serve as scaffolds for bioactive cyclic compounds with a wide range of medicinal applications. 2-((3-Methylbut-2-en-1-yl)oxy)benzaldehyde has been successfully synthesized from 3,3-dimethyl allyl bromide and salicylaldehyde in a 79% yield.  In addition, 2-(4-methyl-3-penteyl)benzaldehyde has been synthesized from <i>o</i>-tolualdehyde and 3,3-dimethyl bromide in a 32% yield.  Both of these aldehydes have been screened for a carbonyl-ene/elimination/Diels-Alder reaction using diphenyl phosphate. Various reaction conditions such as temperature, concentration of aldehyde, solvent, and reaction time have been varied to optimize the domino reaction. These results show that cannabinoid and anthracene derivatives can be made from simple substrates using these sequential reactions.<br/>

Organocatalyzed domino reactions of cannabinoid and anthracene derivatives

2019 Spring National Meeting

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