Journal ArticleDOI
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
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TLDR
In this article, a reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds.Abstract:
The reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds. By the use of DEAD and TPP, diols and hydroxy acids gave cyclic ethers and lactones, respectively. The reaction of nucleosides with DEAD and TPP afforded triphenylphosphoranylnucleosides. Alcohols reacted with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters which converted into the corresponding carbonyl compounds.read more
Citations
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The Palladium-Catalyzed Enyne Cycloisomerization Reaction in a General Approach to the Asymmetric Syntheses of the Picrotoxane Sesquiterpenes. Part I. First-Generation Total Synthesis of Corianin and Formal Syntheses of Picrotoxinin and Picrotin
TL;DR: In this paper, the palladium-catalyzed enyne cycloisomerization is used as a key ring-forming process for the obtention of the cis-fused hydrindane carbon skeleton characteristic of the picrotoxanes sesquiterpenes.
Journal ArticleDOI
Chiral synthons for 2-amino alcohols. Facile preparation of optically active amino hydroxy acids of biological interest.
TL;DR: A promising method for the synthesis of chiral 2-amino alcohols is provided by the enantioselective functionalization of the olefinic moiety of the simple heterocycle, 2-oxazolone, involving a stereodefined introduction of easily replaceable groups followed by stepwise substitution as discussed by the authors.
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Radical cyclizations of acylsilanes in the synthesis of (+)-swainsonine and formal synthesis of (−)-epiquinamide
TL;DR: In this article, polyhydroxylated indolizidine (+)-swainsonine was synthesized through two different bond connection approaches to construct the bicyclic skeleton, using the cyclization as a key step.
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Synthesis of an azobenzene-linker-conjugate with tetrahedrical shape
TL;DR: In this paper, a tripodal linker system with an adamantane core unit and an azobenzene headgroup is reported for the preparation of photochromic SAMs on gold surfaces.
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Tetra-substituted phenyl derivatives
TL;DR: In this article, the authors describe a group of compounds of general formula (STR1) where each compound is a halogen atom, an alkyl group, or a methyl group.
References
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Journal ArticleDOI
Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts
Oyo Mitsunobu,Masaaki Yamada +1 more
TL;DR: In this article, the reaction of carboxylic acid with triphenyl phosphine and diethyl azodicarboxylate in the presence of an alcohol has been studied.
Journal ArticleDOI
Synthesis of lactones and cycloalkanes. Cyclization of ω-hydroxy acids and ethyl α-cyano-ω-hydroxycarboxylates
Journal ArticleDOI
Stereoselective and Stereospecific Reactions. III. Benzoylation, Cyclfzation, and Epimerization of Diols
TL;DR: The benzoylation of various classes of diols by means of diethyl azodicarboxylate and triphenylphosphine was carried out at room temperature as mentioned in this paper.
Journal ArticleDOI
Reaktionen mit phosphororganischen Verbindungen. XLII. Nucleophile Substitutionen an Hydroxysteroiden mit Hilfe von Triphenylphosphan/Azodicarbonsäureester†‡
Hans Loibner,Erich Zbiral +1 more
TL;DR: Nucleophilic substitution reactions of Hydroxysteroids using Triphenylphosphane/diethylazodicarboxylate in benzene was described in this article, where it was not possible to run this substitution process in the hitherto used solvent THF.
Journal ArticleDOI
Eine neue Synthese von (±)-Pyrenophorin
TL;DR: The synthesis of pyrenophorin (I), a 16-membered dilactone metabolite of plant pathogenic fungi is described, which involves removal of the acetal groups and the addition of protected functional groups to the ethylene acetal.
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