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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 ...

APO866 is an inhibitor of nicotinamide adenine dinucleotide (NAD) biosynthesis that exhibits potent anti-lymphoma activity. Rituximab (RTX), an anti-CD20 antibody, kills lymphoma cells by direct apoptosis and antibody- and complement-dependent cell-mediate ...

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 ...

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 ...

Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-lactone type, e.g. prelactones B and E, common in polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy)penta-1,3-dien-3-y ...

The first ene reactions of SO2 and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO2 with alkenes can be used to generate beta,gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of ...

The electrophilic addition of benzeneselenyl chloride to the alkene moiety of 7-azabicyclo[2.2.1]hept-5en-2-yl derivatives has been studied. With camphanates 8 and 9 N-Boc-5-endo-chloro-6-exo-phenylseleno-7-azanorborn-2-yl camphanates 10 and 11 are obtaine ...

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 ...

The exo- and endo-irontricarbonyl complexes of 5,6-dimethylidene-2-exo-norbornyl alcohols 10x, 10n, p-bromobenzenesulfonates 11x, 11n, acetate 12x and of the 2,3-dimethylidene-7-anti-norbornyl alcohols 17x, 17n, p-bromobenzenesulfonates 19x, 19n and acetates 20x, 20n have been prepared. The SN1 buffered acetolyses of 11x, 19x and 19n gave 12x, 20x and 20n, respectively (retention of configuration). The first-order rate constants of the acetolyses have been evaluated and compared with those of the acetolyses

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 ...

Indoleamine 2,3-dioxygenase 1 (IDO1) catalyzes the rate-limiting step in the kynurenine pathway of tryptophan metabolism, which is involved in immunity, neuronal function, and aging. Its implication in pathologies such as cancer and neurodegenerative disea ...

Enantiomerically pure 2,8-diazabicyclo[3.2.1]oct-2-ene derivatives (+)-5 and (-)-5 have been obtained from 2-azido-3-tosyl-7-azabicyclo[2.2.1]heptanes (+)-1 and (-)-2 and their enantiomers, by ring expansion under radical conditions. Compounds (+)-5 and (-)-5 were transformed into hemiaminals 9 ((3S,4R,5R)- and 10 ((3R,4S,5S)-5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidine) that are good inhibitors of alpha-mannosidases. (C) 2003 Published by Elsevier Science Ltd.

The reaction of 1-(trimethylsilyloxy)cyclopentene (9) with (+/-)-1,3,5-triisopropyl-2-(1-(RS)-{[(1E)-2-methylpenta-1,3-dienyl]oxy}e thyl)benzene ((+/-)-4a) in SO2/CH2Cl2 containing (CF3SO2)(2)NH, followed by treatment with Bu4NF and MeI gave a 3.0:1 mixture of (+/-).(2RS)-2-{(1RS,2Z,4SR)-2-methyl)-4-(methylsulfonyl)-1-[(RS)-1-(2,4, 6-triisopropylphenyl)ethoxy]pent-2-en-1-yl}cyclopentanone ((+/-)-10) and (+/-)-(2RS)-2-{(1RS,2Z)-2-methyl-4-[(SR)-methylsulfonyl]-1-[(SR)-1-(2,4, 6-triisopropylphenyl)ethoxy]pent

The ene reaction of sulfur dioxide with enoxysilanes or with allylsilanes generates silyl sulfinates that can be brominated (Br-2 or NBS) or chlorinated (NCS or Cl-2) to produce the corresponding sulfonyl halides. They react with primary and secondary amines or alcohols to give the corresponding sulfonamides and sulfonic esters, respectively. The hetero-Diels-Alder addition of sulfur dioxide to 1-oxy- or 1,3-dioxy-1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfina

The synthesis of a fully deprotected ketimine-type iminosugar is reported, starting from commercial D-mannose diacetonide. An appropriate solvent system was critical for the success of the key tandem addition/cyclization reaction. Reduction of the imine wa ...

The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism. Many IDO1 inhibitors with different chemo ...

Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7- azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxy

The syntheses of azaMan-beta-(1-->6)-C-Glc (4), azaGlc-beta-(1-->6)-C-Glc (5), and azaGal-beta-(1-->6)-C-Glc (6) based upon double reductive amination of acetylenic carbohydrate-derived diketones is described. The required diketones are obtained by addition of the acetylenic sugar anion derived from dibromoolefin 7 to benzyl-protected mannopyranolactone, glucopyranolactone, or galactopyranolactone, followed by reduction of the ketose and oxidation of the resulting diol. Ensuing double reductive amination an

Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-({[(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibi ...

Targeting cancer cells that are highly dependent on the nicotinamide adenine dinucleotide (NAD+) metabolite is a promising therapeutic strategy. Nicotinamide phosphoribosyltransferase (NAMPT) is the rate-limiting enzyme catalyzing NAD(+) production. Despit ...

Pierre Vogel

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

The anti-lymphoma activity of APO866, an inhibitor of nicotinamide adenine dinucleotide biosynthesis, is potentialized when used in combination with anti-CD20 antibody

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

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

Total Asymmetric Syntheses of beta-Hydroxy-delta-lactones via Umpolung with Sulfur Dioxide

BCl3-Mediated Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

The regioselectivity of the addition of benzeneselenyl chloride to 7-azanorborn-5-ene-2-yl derivatives is controlled by the 2-substituent: new entry into 3-and 4-hydroxy-5-substituted prolines

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

Inductive and polarizability effects of an exocyclic diene-iron tricarbonyl group. The acetolyses of exo- and endo-irontricarbonyl complexes of 5,6-dimethylidene-2-exo-norbornyl and 2,3-dimethylidene-7-anti-norbornyl parabromobenzenesulfonates

Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products

Inhibition Mechanisms of Indoleamine 2,3-Dioxygenase 1 (IDO1)

Regioselective rearrangement of 7-azabicyclo[2.2.1]hept-2-aminyl radicals: first synthesis of 2,8-diazabicyclo[3.2.1]oct-2-enes and their conversion into 5-(2-aminoethyl)-2,3,4-trihydroxypyrrolidines, new inhibitors of alpha-mannosidases

One-pot, asymmetric and diastereoselective four-component synthesis of polyfunctional (Z)-alkenyl methyl sulfones with three stereogenic centers

Sulfur dioxide mediated one-pot, three- and four-component syntheses of polyfunctional sulfonamides and sulfonic esters: Study of the stereoselectivity of the ene reaction of sulfur dioxide

Synthesis and L-fucosidase inhibitory potency of a cyclic sugar imine and its pyrrolidine analogue

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

Synthesis of D- and L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline and tripeptides containing them

A short and flexible route to aza-beta-(1 -> 6)-C-disaccharides: Selective alpha-glycosidase inhibitors

Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as alpha-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

Anticancer Activities of Novel Nicotinamide Phosphoribosyltransferase Inhibitors in Hematological Malignancies