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Senior Project submitted to The Division of Science, Mathematics and Computing of Bard College.
Several cannabinoids have been found to have vast potential for medicinal application. One of the less investigated compounds, Cannabicyclol (CBL) can be synthesized in the presence of light via a [2+2] photocycloaddition mechanism. In this photocycloaddition, four and five-membered rings are formed simultaneously. Recent literature has hailed cyclobutanes as rigid scaffolds with potential applications in the fields of chemistry and medicine. This two-step synthesis is initiated using citral and olivetol, two inexpensive and naturally occurring compounds, to form cannabichromene (CBC). The reaction follows an oxa-[3+3] annulation mechanism to form CBC, our targeted photosubstrate. In the subsequent step, chromene is then exposed to a light source where we investigate the [2+2] photocycloaddition to form CBL. The aim of this study is to illuminate efficient and low-cost methods for forming this product and related analogs.
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Oppong-Holmes, Zavontae Edward, "Four Membered Cannabinoid Ring Formation: the Synthesis of Cannabicyclol via [2+2] Photocycloaddition Using UV and Visible Light" (2018). Senior Projects Spring 2018. 69.