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Synthesis of Complex Polycyclic Scaffolds Incorporating α-Amino Esters

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Date Issued:
2015
Summary:
In order to keep up with the high demand for biologically active molecules, chemists devised several synthetic strategies to access novel chemical spaces. The two main strategies to construct new scaffolds are to revisit underexploited or forgotten reactions or to devise new transformations. We are exploring a unique and underexploited reaction, the Himbert–Henn cycloaddition, to produce complex molecular scaffolds in a single step (strategy 1). In a second novel approach, we are modifying the Hantzsch 4-component reaction (4CR) by incorporating an α-amino ester residue to construct new molecules (strategy 2). Both of these reactions have great potential to synthesize novel and chiral molecules from proteinogenic α-amino esters. These unprecedented and complex polycyclic molecules have potential application in medicinal chemistry and natural product synthesis. 4-aza-podophyllotoxins obtained by the Hantzsch-4CR have been proven to be potent as anti-leukemia, anti-colon cancer, and vascular disrupting agents (with nanomolar activity).
Title: Synthesis of Complex Polycyclic Scaffolds Incorporating α-Amino Esters.
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Name(s): Zorc, Stephen A.
Samanta, Shyam S.
Roche, Stéphane P.
Charles E. Schmidt College of Science
Type of Resource: text
Genre: Poster
Date Issued: 2015
Publisher: Florida Atlantic University Libraries: Digital Library
Physical Form: pdf
Extent: 1 p.
Language(s): English
Summary: In order to keep up with the high demand for biologically active molecules, chemists devised several synthetic strategies to access novel chemical spaces. The two main strategies to construct new scaffolds are to revisit underexploited or forgotten reactions or to devise new transformations. We are exploring a unique and underexploited reaction, the Himbert–Henn cycloaddition, to produce complex molecular scaffolds in a single step (strategy 1). In a second novel approach, we are modifying the Hantzsch 4-component reaction (4CR) by incorporating an α-amino ester residue to construct new molecules (strategy 2). Both of these reactions have great potential to synthesize novel and chiral molecules from proteinogenic α-amino esters. These unprecedented and complex polycyclic molecules have potential application in medicinal chemistry and natural product synthesis. 4-aza-podophyllotoxins obtained by the Hantzsch-4CR have been proven to be potent as anti-leukemia, anti-colon cancer, and vascular disrupting agents (with nanomolar activity).
Identifier: FA00005218 (IID)
Subject(s): College students --Research --United States.
Persistent Link to This Record: http://purl.flvc.org/fau/fd/FA00005218
Host Institution: FAU