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Pierre Vogel

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Related publications (99)

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

Pyrrolidine derivatives as new inhibitors of alpha-mannosidases and growth inhibitors of human cancer cells

Pierre Vogel, Sandrine Gerber, Hélène Fiaux

New pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L(+)-phenylglycinol and tested for their ability to inhibit 25 commercial glycosidases. The influence of the substitution of the lateral side chain and of the pyrrolidine ring on the enzyme ...

2006

Trifluoromethanesulfonyl chloride, first update

Pierre Vogel, Sandrine Gerber

2006

The bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters. New route to sulfoxides

Pierre Vogel, Adrien Keith Lawrence, Maris Turks

A new one-pot synthesis of sulfoxides is presented. It involves the bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters, giving mixed anhydrides of sulfinic and boric acids. The latter react chemoselectively at the sulfur center with Grigna ...

Elsevier2006

C(1 -> 4)-linked disaccharides through carbonylative Stille cross-coupling

Pierre Vogel, Peter Steunenberg

A tinglucal tributyl[4,6-O-bis(t-butyl)silylidene-3-O-tris(isopropyl)silyl]tin 7 and a triflate derived from isolevoglucosenone (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate 10 undergo the carbonylative Stille conden ...

2005

Expeditious asymmetric synthesis of a stereoheptad corresponding to the C(19)-C(27)-ansa chain of rifamycins: Formal total synthesis of Rifamycin S

Pierre Vogel, Xiaogen Huang, Maris Turks

In the presence of sulfur dioxide and an acid promoter, (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenyleth- oxy)penta-1,3-dien-3-yl isobutyrate reacts with (Z)-3-(trimethylsilyloxy)-pent-2-ene giving a silyl sulfinate intermediate that undergoes, in the presence of ...

2005

Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics

Pierre Vogel

The syntheses of new C8-carbasugars and -aminocyclitols related to miglitol and voglibose are described. The key step involves the ring closing metathesis of 1,9-dienes derived from D-mannitol. Chemical transformations of the newly created double bond of t ...

2005

Synthesis of aza-C-disaccharides (dideoxyimino-alditols C-linked to monosaccharides) and analogues

Pierre Vogel, Inmaculada Robina

The first aza-C-disaccharide (D-azaMan-beta-CHz-(1 -> 6)-D-Man-alpha-OMe) that mimicks alpha-D-Manp-(1 -> 6)-alpha-D-ManOMe was made in 1994 by Johnson and coworkers. Several synthetic approaches to these disaccharide mimetics have been proposed. These are ...

Georg Thieme Verlag2005

One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)->(E) isomerization induced by sulfur dioxide

Pierre Vogel

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization b ...

2005

New 1-amino-1-deoxy- and 2-amino-2-deoxy-polyhydroxyazepanes: synthesis and inhibition of glycosidases

Pierre Vogel, Eliazar Rodriguez Garcia

Eight new seven-membered ring iminoalditols, displaying an amino group and a hydroxymethyl group on the ring, have been synthesized from D-arabinose via epoxidation of a protected azacycloheptene and subsequent nucleophilic opening. Three of them show a po ...

2005

C-linked disaccharide analogue of the Thomsen-Friedenreich (T)-epitope alpha-O-conjugated to L-serine

Pierre Vogel, Loay Awad

Condensation of a silylated beta-D-galactopyranosylaldehyde (3) with isolevoglucosenone (4) in the presence of Et(2)AII provided bicyclic enone 5. Subsequent addition of BnNHOMe gave adduct 6, which was converted into 4-O-acetyl-1,6-anhydro-3-C-[ R)1.3,4,5 ...

2005

Palladium-catalyzed desulfitative Mizoroki-Heck couplings of sulfonyl chlorides with mono- and disubstituted olefins: Rhodium-catalyzed desulfitative heck-type reactions under phosphine- and base-free conditions

Pierre Vogel

New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoromethanesulfonyl chlorides. Thus (E)1,2-disubstituted alkenes with high stereoselectivi ...

2005

Sulfur dioxide-mediated syntheses of polyfunctional alkenes and (E,Z)- and (E,E)-2,4-dien-1-ones

Pierre Vogel, Laure Bouchez, Cotinica Craita

Efficient methods for the stereoselective synthesis of polyfunctional (E)- and (2)-alkenes and conjugated (EE)- and (E,2)-dienones are presented. They rely upon one-pot, four-component processes that condense 1-oxy-1,3-dienes, silyl enol ethers, SO2, and c ...

2005

New concise total synthesis of (+)-lentiginosine and some structural analogues

Pierre Vogel

An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural anal ...

2005

Noniterative approach to the total asymmetric synthesis of 15-carbon polyketides and analogs with high stereodiversity

Marc-Etienne Schwenter, Kai Torsten Meilert, Pierre Vogel, Sandrine Gerber

Starting from inexpensive furan and furfuryl alcohol, a noniterative approach to the synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives has been developed. The method relies upon the double [4+3]-cycloaddition of 1,1,3-trichloro-2-oxyla ...

2005

Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids

Pierre Vogel, Loay Awad, Xiaogen Huang, Cotinica Craita

Alcohols, phenols and carboxylic acids are silylated with very good yields in the presence of silyl methallylsulfinates under non- basic conditions and with the formation of volatile co-products. ...

Royal Society of Chemistry2005

Synthesis of the C(1)-C(11) polyene fragment of apoptolidin with a new sulfur dioxide-based organic chemistry

Pierre Vogel, Laure Bouchez

A new sulfur dioxide-based organic chemistry has been developed as a novel approach for the stereoselective synthesis of polyene fragments based on our one-pot, four-component synthesis of polyfunctional alpha-alkanesulfonyl-gamma,delta-unsaturated ketones ...

2005

Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are beta-glucosidase inhibitors

Pierre Vogel

The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAC)(3). The N-subst ...

2005

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

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