The Development of Synthetic Methods Using Isoindole Chemistry

Graduate Thesis Or Dissertation

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Citeable URL: https://scholar.colorado.edu/concern/graduate_thesis_or_dissertations/cf95jd004

Abstract

Isoindoles are very reactive 10π aromatic heterocycles that commonly act as nucleophiles. Isoindole derivatives, which can be accessed via isoindoles, are ubiquitous in natural products and synthetic bioactive molecules. This dissertation presents a review of recent literature involving isoindole chemistry and describes the development of synthetic methods that utilize isoindole chemistry. First, a review of the literature from the past decade (2012-present) pertaining to the synthesis and reactions of isoindoles is given. Second, a novel one-pot synthesis of polycyclic isoindolines is described which employs an innovative isoindole umpolung strategy that allows isoindoles, which typically act as nucleophiles, to be used instead as electrophiles in a Pictet-Spengler-type cyclization. This method extends the scope of the Pictet-Spengler reaction to include isoindoles and affords the polycyclic isoindoline products in good yields. Third, efforts toward the development of two cyclization cascade reactions that involve isoindole chemistry are described, which provide access to analogs of batracylin, a versatile anticancer drug, and tryptanthrin, an antimicrobial and antiviral agent.

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