Search results for "DISCOVERY"
showing 10 items of 4119 documents
Cycloalkin-vinylidencycloalkan-umlagerungen
1989
Abstract Flash pyrolysis of the strained cyclic alkynes 1 leads to ring systems 2 with an exocyclic allene group and in a further isomerization step to the conjugated vinyl compounds 3 .
Solid-Phase Synthesis of a Sialyl-Tn-Glycoundecapeptide of the MUC1 Repeating Unit
1997
The synthesis of glycopeptides carrying tumour-associated antigens is of interest for cancer diagnosis and treatment. Here, a very efficient route lo disaccharide threonine building block 8 is presented which allows the introduction of the sialyl-Tn antigen into a peptide. The syntheses of the undecapeptide and the sialyl-Tn-containing glycoundecapeptide, which are a part of the repeating unit of MUC1, were performed by solid-phase synthesis with an allylic anchor cleavable under neutral conditions. After detachment from the resin, the peptide and the glycopeptide arc completely deprotected giving the target compounds 13 and 15, respectively.
Photochemical Functionalization of Allyl Benzoates by C-H Insertion
2013
The photoreactivity of allyl benzoates, containing an electron-rich double bond, has been explored by irradiation at 305 nm in different solvents. Solvent addition products arising from an insertion of the alpha H–C bonds of THF, dioxane, and i-PrOH to the allylic double bond was realized. The observed reactivity depended on reaction conditions and substitution pattern of the substrate. A DFT study on this unusual reaction was performed allowing the formulation of two mechanistic pathways.
Fragment condensation on solid-phase in the synthesis of an amphiphilic glycopeptide from the homophilic recognition domain of epithelial cadherin 1
1998
Abstract The lipo-glycopeptide 6 containing the homophilic recognition motif of mouse epithelial cadherin 1 was synthesised via a fragment condensation on a solid phase linked peptide using an allylic anchor and a pentafluorophenol-based coupling reagent.
A stereoselective synthesis of (+)-malyngolide via a ring-closing olefin metathesis
2000
Abstract A very short and stereoselective synthesis of the non-natural enantiomer of malyngolide from l -erythrulose is described. Key features of the synthesis are the Felkin–Anh diastereoselective allylation of a polyoxygenated ketone and the allylation/metathesis/allylic oxidation protocol recently described by our group.
Semisynthesis of new tetrahydrofuranic alkyl ester and furano-pyrone derivatives as inhibitors of the mitochondrial complex I
2002
Abstract Methoxymethylation of altholactone ( 1 ) led to the corresponding O -methoxymethyl derivative ( 3 ) in addition to the unexpected 6,7-dihydro-7-methoxy analogue ( 4 ), and two original tetrahydrofuranic (THF) alkyl esters ( 5 , 6 ). Moreover, when we accomplished a new method for the preparation of the furano-pyrone goniofupyrone ( 7 ) through 7-hydroxylation of 1 in acid medium, a minor compound ( 8 ) with an identical skeleton to that of compounds 5 and 6 was identified. Careful examination of the published spectral data of the reported styryl-lactones with an heptolide skeleton reveals that those structures possess also a THF alkyl ester skeleton. The revision of those structure…
A novel synthesis of chain-extended amino sugar derivatives through aza-Cope rearrangement of N-galactosyl-N-homoallylamines
1998
Abstract Chain-extended amino sugars are synthesized via stereocontrolled Lewis acid-catalyzed aza-Cope rearrangement of N-glycosyl homoallylamines in high yield and stereoselectivity.
Dienediolates of unsaturated carboxylic acids in synthesis. Synthesis of cyclohexenones and polycyclic ketones by tandem Michael-Dieckmann decarboxyl…
1994
Abstract Substituted 2-cyclohexenones 4 to 7 and hexaxydronaphthalenones and hexahydroindenones 13 to 18 are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of acyclic and alicyclic unsaturated carboxylic acids to the lithium salts of the same or other unsaturated carboxylic acids.
Reductive transformations - 11. stereoselective cycloannelation and bridging of the cyclooctatetraene dianionMakromol. Chem., Rapid. Commun. 1988, 9,…
1988
Abstract Bifunctional electrophiles with C4-, C6-, and C8-chains are reacted with the cyclooctatetraene dianion to selectively give novel cycloannelation and bridging products which possess a surprising stereochemistry and are useful starting compounds for further syntheses.
Two new triterpene saponins from Eryngium campestre.
2005
Two new triterpene saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-angeloyl-R1-barrigenol (1) and 3-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucuronopyranosyl-22-O-beta,beta-dimethylacryloyl-A1-barrigenol (2), were isolated from the roots of Eryngium campestre (Apiaceae). Their structures were established mainly by 2D NMR techniques and mass spectrometry.