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The Synthesis of Lysergic Acid via a Photoelectrocyclization

Year: 2023

Presenter Name: Aidan Connor

Cyclizations are important reactions in organic chemistry (1). They can create cyclic and polycyclic structures in a single transformation and are widely used in the chemical industry (2,4). Electrocyclization reactions, a particular type of cyclization reaction, can be initiated using thermal or photochemical conditions (like UV light). Controlling these conditions can lead to the generation of multiple bonds, often with high diastereoselectivity. Currently, the main method to synthesize phenanthrene systems, which are polycyclic aromatic carbons, involves using heavy metal reagents, such as Grubbs catalysts for metathesis reactions (6). Since photochemical reactions use light as their reagent, they can be a useful workaround for the synthesis of these systems, which helps to minimize unnecessary reagents or hazardous waste. While photochemical reactions have been studied since the 1960s for the synthesis of phenanthrene (5), recently the Rainier group has expanded on the use of these reactions to synthesize more complex derivatives of 8,9-dihydrophenanthrenes (3). Further study could increase the current scope of photochemical electrocyclizations to cover a broad range of complex systems and potentially lead to more efficient syntheses of a variety of natural products. Additionally, the synthesis and experimentation of these more complex systems could lead to a deeper understanding of the fundamental electrocyclization reactivity. For this research project, I specifically plan on using photochemical electrocyclizations in an attempt to synthesize Lysergic Acid. Lysergic Acid is a precursor to many important drugs that are used to treat depression, anxiety, and addiction (7). Currently, complex synthesis methods are necessary to produce Lysergic Acid, if the ability to use UV light as a reagent was discovered, the chemical process of synthesizing Lysergic Acid would be greatly simplified.
University / Institution: University of Utah
Type: Poster
Format: In Person
Presentation #C81
SESSION C (1:45-3:15PM)
Area of Research: Science & Technology
Faculty Mentor: Jon Rainier