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Synthèse totale énantiosélective de la (11R)-(-)-8-épi-11-hydroxy-aphidicoline par réactions de Diels-Alder/aldol transannulaires en tandem
(Université de Sherbrooke, 1999)
Au cours de cette thèse, nous verrons la synthèse totale de la (11R )-(-)-8-épi-11-hydroxy-aphidicoline et toutes les recherches pour y arriver. Le présent ouvrage sera divisé en quatre grandes parties. Dans un premier ...
Studies toward total synthesis of (±)-caldaphnidine C via one-pot sequential intramolecular Vilsmeier–Haack and azomethine ylide 1,3-dipolar cycloaddition
(2016)
An application of a one-pot sequential Vilsmeier–Haack cyclization and intramolecular azomethine ylide 1,3-dipolar cycloaddition toward the total synthesis of (±)-caldaphnidine C is presented. It allowed an efficient ...
Bis-michael acceptors as novel probes to study the Keap1/Nrf2/ARE pathway
Other titre : Supporting information for "Bis-michael acceptors as novel probes to study the Keap1/Nrf2/ARE pathway"
(2016)
Nuclear factor erythroid 2-related factor 2 (Nrf2) is a master regulator that promotes the transcription of cytoprotective genes in response to oxidative/electrophilic stress. Various Michael-type compounds were designed ...
Preparation of conformationally restricted β2,2- and β2,2,3-amino esters and derivatives containing an all-carbon quaternary center
(2015)
Abstract: β-Amino acids are routinely incorporated into peptidic drugs to increase their stability and to incur conformational biases. However, the synthesis of highly substituted β-amino acids still represents a great ...
Highly diastereoselective synthesis of substituted pyrrolidines using a sequence of azomethine ylide cycloaddition and nucleophilic cyclization
(2010)
Abstract: Although cycloadditions of azomethine ylides usually give mixtures of endo/exo adducts, we successfully tuned the mechanistic path of a new reaction cascade to afford substituted pyrrolidines in high yields and ...
Short approach toward the nonracemic A,B,E tricyclic core of calyciphylline B-type alkaloids
(2017)
Abstract: A suitably functionalized tricyclic adduct containing the common A,B,E rings found in calyciphylline B-type alkaloids was obtained in nine linear steps. The key transformation features an efficient one-pot sequence ...
General approach toward aspidospermatan-type alkaloids using one-pot Vilsmeier–Haack cyclization and azomethine ylide cycloaddition
(2017)
Abstract: The development of a new one-pot reaction sequence afforded the tricyclic core of several aspidospermatan-type alkaloids from a linear, densely functionalized substrate. The key sequence features a highly ...
Synthesis of the tetracyclic core of daphnilactone B-type and yuzurimine-type alkaloid
(2011)
Abstract: The core of daphnilactone B-type and yuzurimine-type alkaloids was synthesized in only 16 steps from a known β-allyl-γ-butyrolactone. The key sequence of Vilsmeier–Haack cyclization and intramolecular azomethine ...
Asymmetric total synthesis of (+)-virosine a via sequential nucleophilic cyclizations onto an activated formamide
(2012)
Abstract: The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using ...
Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine
(2006)
Abstract: Vilsmeier-Haack type cyclizations proved to be particularly efficient for generating parts of the polycyclic
cores of many alkaloids, although only monocyclizations have so far been reported. With the goal ...