Presentation Title

Synthesis of Psychrophilin E Using N-Heterocyclic Acyl Electrophiles

Faculty Mentor

Stephen T. Heller

Start Date

17-11-2018 12:30 PM

End Date

17-11-2018 2:30 PM

Location

CREVELING 2

Session

POSTER 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Psychrophilin E, a cyclic tripeptide, is naturally derived from two marine fungal strains of the genus Aspergillus and is known to have anti-proliferative properties toward certain colon cancer cells (Ebada, et. al, 2013). Because of its anti-proliferative properties, Psychrophilin E is an attractive target for total synthesis. A one-pot sequential chemoselective amidation has been identified as a possible strategy for the efficient synthesis of Psychrophilin E. To this end, an N-acylbenzotriazole derivative of anthranilic acid was successfully coupled to the indole nitrogen of derivatives of L-tryptophan. A fluorinated variant of anthranilic acid was used to monitor the progress of these amidation reactions by 19F NMR. Recent and future experiments on the coupling of N-acyltryptophan intermediates with an acylimidazole derivative of proline will also be discussed, as will tactics for the macrolactamization of the linear precursor of Psychrophilin E.

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Nov 17th, 12:30 PM Nov 17th, 2:30 PM

Synthesis of Psychrophilin E Using N-Heterocyclic Acyl Electrophiles

CREVELING 2

Psychrophilin E, a cyclic tripeptide, is naturally derived from two marine fungal strains of the genus Aspergillus and is known to have anti-proliferative properties toward certain colon cancer cells (Ebada, et. al, 2013). Because of its anti-proliferative properties, Psychrophilin E is an attractive target for total synthesis. A one-pot sequential chemoselective amidation has been identified as a possible strategy for the efficient synthesis of Psychrophilin E. To this end, an N-acylbenzotriazole derivative of anthranilic acid was successfully coupled to the indole nitrogen of derivatives of L-tryptophan. A fluorinated variant of anthranilic acid was used to monitor the progress of these amidation reactions by 19F NMR. Recent and future experiments on the coupling of N-acyltryptophan intermediates with an acylimidazole derivative of proline will also be discussed, as will tactics for the macrolactamization of the linear precursor of Psychrophilin E.