Work

Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin

Year: 2017

Type: article

Abstract: The synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product, is described. The synthesis starts with the diketopiperazine nucleus intact and the side chains are installed using iterative aldol condensations. The route represents a general strategy for synthesis of a wide array of mono-alkylidene diketopiperazine structures, including those derived from non-canonical amino acid residues.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c7ob02297b

Authors: Elizabeth W. Kelley, Skylar G. Norman, Jonathan R. Scheerer

Institution: William & Mary

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Camille and Henry Dreyfus Foundation, National Institutes of Health, National Institute of General Medical Sciences

Award: New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines