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New Organic reactions and their application to the synthesis of natural compounds and analogues of interest for the chemotherapy of cancer and infectious diseases

English title New Organic reactions and their application to the synthesis of natural compounds and analogues of interest for the chemotherapy of cancer and infectious diseases
Applicant Vogel Pierre
Number 116212
Funding scheme Project funding (Div. I-III)
Research institution Institut des sciences et ingénierie chimiques EPFL - SB - ISIC
Institution of higher education EPF Lausanne - EPFL
Main discipline Organic Chemistry
Start/End 01.04.2007 - 31.03.2009
Approved amount 539'981.00
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Keywords (30)

catalysis; asymmetric synthesis; glycochemistry; anti-cancer agents; anti-cancer vaccine; apoptolidine; New reaction cascades; organic catalysis; antibiotics; glycosidase inhibitors polyketides; sugar mimetics; Brasinolide; Apoptolidin; Spongistatin; combinatorial synthesis; dienes; glycomimetics; glycosidase inhibitors; glycosyltransferase; ene-reactions; hetero-Diels-Alder additions; natural products; new C-C bond forming reactions; new catalysts; one-pot synthesis of stereotriads of stereotetrads; pericyclic reactions of sulfur dioxide; polyketides; polypropionates; reaction cascades; stereoselective and stereodivergent syntheses

Lay Summary (English)

Lead
Lay summary
Starting from furans, inexpensive compounds obtained from the left overs of agriculture, complicated polyketides fragments part of important anti-tumor (e.g.: Spongistatins) and antibiotics have been obtained. Bulk sulfur dioxide cost less than CHF 0.30 per kilo. We use it as recoverable solvent, reagent and catalyst in a new organic chemistry that allows one to prepare in a few steps complicated polypropionates fragments found in several natural antibiotics (erythromycin) and anti-tumor compounds (apoptolidin). New reactions and reaction cascade have been invented such as iron-catalyzed desulfinylative C-C cross coupling using sulfonyl chlorides as electrophiles. Tamiflu is an example of sugar mimetic. We have prepared several monosaccharide and disaccharide mimetics and evaluated their biological activity. Thus, new antitumor agents have been discovered that are 3,4-dihydroxypyrrolidine derivatives.
Direct link to Lay Summary Last update: 21.02.2013

Responsible applicant and co-applicants

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Associated projects

Number Title Start Funding scheme
108105 New Organic Chemistry of Sulfur Dioxide 01.04.2005 Project funding (Div. I-III)
124724 New Organic Chemistry of Sulfur Dioxide and the synthesis of anti-biotics 01.04.2009 Project funding (Div. I-III)
121262 R'Equip - Amélioration de deux spectromètres RMN 9.4T par des consôles digitales 01.07.2008 R'EQUIP
124724 New Organic Chemistry of Sulfur Dioxide and the synthesis of anti-biotics 01.04.2009 Project funding (Div. I-III)

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