Project

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Asymmetric Indolone-Malonate Coupling Reaction: Application to the Synthesis of the Communesin Alkaloids

Applicant Lapointe Guillaume
Number 141444
Funding scheme Fellowships for prospective researchers
Research institution Division of Chemistry and Chemical Engineering California Institute of Technology
Institution of higher education Institution abroad - IACH
Main discipline Organic Chemistry
Start/End 01.03.2012 - 31.08.2013
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Keywords (10)

communesin; leukemia; indolone; asymmetric; catalytic; synthesis; alkaloid; coupling; microfilament-disruption; catalytic synthesis

Lay Summary (English)

Lead
Lay summary
The objective of this research project is to execute a catalytic enantioselective synthesis of the communesin alkaloids using the asymmetric indolone-malonate coupling reaction developed in the laboratory of professor B. M. Stoltz. The highly functionalized polycyclic skeleton of these alkaloids, along with its two continguous quaternary centers and its two aminal moieties make the communesins synthesis a daunting challenge. This challenge is only equalled by their formidable biological activity, such as being cytotoxic to P-388 lymphoid leukemia cells and being an efficient microfilament disruptor.
Direct link to Lay Summary Last update: 21.02.2013

Responsible applicant and co-applicants

Scientific events

Active participation

Title Type of contribution Title of article or contribution Date Place Persons involved
43rd National Organic Chemistry Symposium 23.06.2013 University of Washington, Seattle, USA
Bayer Postdoc Workshop 2013 01.06.2013 Long Island, New York, USA


Abstract

The objective of this research project is to execute a catalytic enantioselective synthesis of the communesin alkaloids using the asymmetric indolone-malonate coupling reaction developed in the laboratory of professor B. M. Stoltz. The highly functionalized polycyclic skeleton of these alkaloids, along with its two continguous quaternary centers and its two aminal moieties make the communesins synthesis a daunting challenge. This challenge is only equalled by their formidable biological activity, such as being cytotoxic to P-388 lymphoid leukemia cells and being an efficient microfilament disruptor.
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