Arene-alkene cycloadditions and organic synthesis

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Abstract
Factors influencing the selectivities of the arene-alkene photo-cycloaddition have been investigated in connection with the application of this process in complex molecule synthesis. Described herein are syntheses of silphinene, subergorgic acid, retigeranic acid, and a grayanotoxin I1 precursor based on this process. The discovery of a new cycloaddition based on 4-pyrones is also summarized. Arene-alkene photo-cycloadditions (Scheme 1) are among the most powerful and versatile strategy level reactions for complex molecule synthesis. Discovered over a period of a decade beginning in the late 1950's, these remarkable reactions have attracted considerable mechanistic and theoretical interest, leading in recent years to spectacular applications in synthesis.1 This lecture is designed to provide. an overview of recent advances in this field with an emphasis on the development of the arene-alkene cycloaddition as a tool for the rational synthesis of complex molecules.

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