Presentation Title

Assessment of a Cyclodearomatization Approach to Construct the Tricyclic Core of Swerilactone A

Faculty Mentor

Raul Navarro

Start Date

23-11-2019 10:00 AM

End Date

23-11-2019 10:45 AM

Location

249

Session

poster 3

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Herein, a concise synthesis of the biologically active natural product swerilactone A is proposed. Our synthetic strategy hinges on the development of a nucleophilic dearomatization reaction to install one of the two all-carbon quaternary stereocenters, followed by acid-catalyzed cyclization cascade to generate the pentacyclic core of the natural product. More specifically, the goal of this report was to optimize a reaction sequence previously developed by our research group to more efficiently access a properly functionalized dearomatization precursor, and to thoroughly explore a metal-catalyzed nucleophilic dearomatization reaction to afford a 10-membered macrocyclic intermediate en route to the natural product. Ultimately, successful execution of this proposal introduces novel methodologies to generate complex rings in total synthesis efforts and will constitute the first total synthesis of swerilactone A.

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Nov 23rd, 10:00 AM Nov 23rd, 10:45 AM

Assessment of a Cyclodearomatization Approach to Construct the Tricyclic Core of Swerilactone A

249

Herein, a concise synthesis of the biologically active natural product swerilactone A is proposed. Our synthetic strategy hinges on the development of a nucleophilic dearomatization reaction to install one of the two all-carbon quaternary stereocenters, followed by acid-catalyzed cyclization cascade to generate the pentacyclic core of the natural product. More specifically, the goal of this report was to optimize a reaction sequence previously developed by our research group to more efficiently access a properly functionalized dearomatization precursor, and to thoroughly explore a metal-catalyzed nucleophilic dearomatization reaction to afford a 10-membered macrocyclic intermediate en route to the natural product. Ultimately, successful execution of this proposal introduces novel methodologies to generate complex rings in total synthesis efforts and will constitute the first total synthesis of swerilactone A.