Synthèse d'inhibiteurs mixtes réversibles de l'AchE par Click Chemistry in-situ

ROUEN-INSA Madrillet (765752301) / SudocSudocFranceF

Total syntheses of echinopines A and B, sesquiterpenes with a unique tetracyclic [3-5-5-7] skeleton

International audienc

Asymmetric Sharpless Dihydroxylation Reaction of Chiral Bishomoallylic Alcohols: Application to the Synthesis of the C1–C10–C5 Fragment of FR225654

International audienc

Synthesis and structure–activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors

International audienc

Asymmetric synthesis of a highly functionalized enantioenriched system close to thapsigargin framework

International audienc

Relative Stereochemical Determination and Synthesis of the C17–C25 δ-Lactone Fragment of Hemicalide

International audienc

Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A

International audienc

Versatile Access to Martin's Spirosilanes and Their Hypervalent Derivatives

International audienceA new route to Martins spirosilanes has been devised. The original synthesis does not allow diversely substituted spirosilane derivatives to be synthesized, and thus their corresponding silicates. In this report, Martins spirosilanes bearing alkyl, aryl, halogen, alkoxy, and trifluoromethyl substituents on the aryl ring have been prepared through a versatile four-step route. Addition of fluoride onto these Lewis acids as a prototypical reaction with a nucleophile yielded a library of stable fluorosilicates. Both sets of compounds have been characterized by X-ray crystallograp

Alkoxyallene-ynes: Selective Preparation of Bicyclo[5.3.0] Ring Systems Including a δ-Alkoxy Cyclopentadienone

International audienc

Relative Stereochemical Determination and Synthesis of the C17–C25 δ‑Lactone Fragment of Hemicalide

Hemicalide is a novel marine metabolite polyketide distinguished by a unique mechanism of action. Because of insufficient quantities of purified material, this natural product has evaded complete stereochemical assignments. Recently, we have determined the relative stereochemistry of the C8–C13 hexad by synthesizing the C1–C13 fragment. Presently, we report the assignment of the C17–C25 δ-lactone fragment. NMR analysis of authentic hemicalide along with a computational conformation study allowed us to reduce the number of putative relative isomers from 16 to 4. Concise syntheses of the four candidate diastereomers were achieved using a common strategy based on a Dias aldehyde allylation reaction, an intramolecular Horner–Wadsworth–Emmons olefination, and a dihydroxylation reaction. Finally, thorough NMR comparisons enabled us to deduce the relative stereochemistry of the C1–C17 fragment with high certainty