85694-06-0Relevant academic research and scientific papers
Exploring the Chemistry of Bicyclic Isoxazolidines for the Multicomponent Synthesis of Glycomimetic Building Blocks
Hoogenboom, Jorin,Lutz, Martin,Zuilhof, Han,Wennekes, Tom
, p. 8826 - 8836 (2016)
Starting from a chiral furanone, the nitrone-olefin [3 + 2] cycloaddition can be used to obtain bicyclic isoxazolidines for which we report a set of reactions to selectively modify each functional position. These synthetically versatile bicyclic isoxazolidines allowed us to obtain complex glycomimetic building blocks, like iminosugars, via multicomponent chemistry. For example, a library of 20 pipecolic acid derivatives, a recurring motif in various prescription drugs, could be obtained via a one-pot Staudinger/aza-Wittig/Ugi three-component reaction of a bicyclic isoxazolidine-derived azido-hemiacetal. Notably, specific pipecolic acids in this library were obtained via hydrolysis of an unique tricyclic imidate side product of the Ugi reaction. The azido-hemiacetal was also converted into an aza-C-glycoside iminosugar via an unprecendented one-pot Staudinger/aza-Wittig/Mannich reaction.
Synthesis of Methyl (1R,2S)-2-cyclopropanecarboxylate: a Potential Inhibitor of the Enzyme 5-Lipoxygenase
Butler, Paul I.,Clarke, Trafford,Dell, Colin,Mann, John
, p. 1503 - 1508 (2007/10/02)
We describe the synthesis of a novel cyclopropyl analogue of arachidonic acid via a convergent synthesis that employed methyl (1R,2S)-2-formylcyclopropanecarboxylate in conjunction with the ylide from (3Z,6Z)-pentadeca-3,6-dienyl(triphenyl)phosphonium iod
A Facile and General Entry to Optically Active Pheromones and Aromas With γ-Alkyl-γ-lactone Structures. A Study of Some Lactone Derivatives of Pentoses
Cardellach, J.,Font, J.,Ortuno, R. M.
, p. 327 - 331 (2007/10/02)
A new and easy general methodology has been developed to prepare γ-alkyl-α,β-butenolides or γ-alkylbutyrolactones in four and five steps, respectively, from D-ribonolactone as a common chiral starting material.Some of these products have pheromonal activity in insects and are also used as fruit fragrances.A study on several derivatives of D-ribonolactone and 2-deoxy-D-ribonolactone has been carried out in order to explore alternative routes for these syntheses.
STUDIES ON STRUCTURALLY SIMPLE α,β-BUTENOLIDES-II (-)-(S)-γ-HYDROXYMETHYL-α,β-BUTENOLIDE AND DERIVATIVES FROM D-RIBONOLACTONE EFFICIENT SYNTHESIS OF (-)-RANUNCULIN
Camps, P.,Cardellach, J.,Font, J.,Ortuno, R. M.,Ponsati, O
, p. 2395 - 2402 (2007/10/02)
A short synthesis of the title compound, 16, from D-ribonolactone is described.Two alternative approaches differing in the timing of the C=C double bond creation are used to prepare some chiral derivatives of 16. (-)-Ranunculin, a glycoside present in Ranunculaceae, has been synthetized for the first time.
