Publications de Sylvain Favre | EPFL Graph Search

Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors

Four branched tetra- and pentahydroxylated azepanes have been synthesized from a common azepane precursor through dihydroxylation followed by deoxygenation. They have been assayed as glycosidase inhibitors on a panel of 22 glycosidases and one methylated a ...

2012

Synthetic studies toward the CD spiroketal of spongistatins

Pierre Vogel, Sandrine Gerber, Sylvain Favre

Starting from the readily available meso-methylenedi(8-oxa-3-oxobicyclo[3.2.1]hept-6-en-1-yl) (1), meso-1,1'-methylidene [(4R,4'S,6R,6'S)-4,6-dioxycyclohept-1-en-1-yl]tetrasilylethers (7, 8) were obtained and transformed into all-syn 1,3,5,11,13,15-hexahyd ...

Wiley-Blackwell2010

New efficient synthetic strategies towards the AB and CD spiroketal fragments of spongistatins and analogues

Sylvain Favre

For thousands of years, nature provided us remedies to treat diseases and its biologically active molecules inspired chemists for the development of new drugs. In 1993, three research groups independently reported the isolation, from sponges, of spongistat ...

EPFL2009

New synthetic seven-membered 1-azasugars displaying potent inhibition towards glycosidases and glucosylceramide transferase

Pierre Vogel, Sylvain Favre, Claudia Bello, Tao Liu

Several members of a new family of seven-membered azasugars, which can be seen as 1-azasugar ring homologues, have been I obtained by simple chemical transformations starting from a sugar-derived azidolactol. Unlike their piperidine counterparts, these mol ...

2008

Preparation and synthetic applications of 8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives

Pierre Vogel, Sandrine Gerber, Sylvain Favre

The development of efficient routes to multi gram quantities of chiral synthons is a key issue in total synthesis of natural products and analogues. The conformationally defined and rigid 8-oxabicyclo[3.2.1]oct-6-en-3-one template appears as an appealing s ...

2008

Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products

Pierre Vogel, Sandrine Gerber, Sylvain Favre

Many natural products of biological interest contain [6,5]- and [6,6]-spiroketal moieties that can adopt various configurations, benefiting or not from anomeric conformation stabilizing effects. The spiroketal fragments are often important for the biologic ...

2008

New efficient route to an advanced precursor of the AB spiroketal of spongistatins

Pierre Vogel, Sandrine Gerber, Sylvain Favre

2007

Synthesis of new pyrrolidine derivatives as inhibitors of alpha-mannosidase and of glioblastoma cells growth

Pierre Vogel, Sandrine Gerber, Sylvain Favre, Hélène Fiaux

New 2-benzylamino-3,4-dihydroxypyrrolidines bearing aromatic and aliphatic amido side chains have been prepared. The influence of the amido substituents on the inhibitory activity of these diamines toward 24 commercially available glycosidases was determin ...

2006

Functionalized pyrrolidines as alpha-mannosidase inhibitors and growth inhibitors of human glioblastoma and melanoma cells

Pierre Vogel, Sandrine Gerber, Sylvain Favre, Hélène Fiaux

New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases wer ...

2005