16139-79-0Relevant articles and documents
Combining two-directional synthesis and tandem reactions: A short formal synthesis of halichlorine
Gignoux, Camille,Newton, Annabella F.,Barthelme, Alexandre,Lewis, William,Alcaraz, Marie-Lyne,Stockman, Robert A.
, p. 67 - 69 (2012)
A short and efficient synthesis of an advanced intermediate (1) in the Clive route to halichlorine has been achieved in 12 steps and 13.2% yield by a combined two-directional synthesis/tandem reaction strategy.
Detection of a New Piperideine Alkaloid in the Pygidial Glands of Some Stenus Beetles
Wittmann, Isabel,Schierling, Andreas,Dettner, Konrad,G?hl, Matthias,Schmidt, Jürgen,Seifert, Karlheinz
, p. 1422 - 1434 (2015)
Rove beetles of the genus Stenus produce and store bioactive alkaloids like stenusine (3), 3-(2-methylbut-1-enyl)pyridine (4), and cicindeloine (5) in their pygidial glands to protect themselves from predation and microorganismic infestation. The biosynth
Intramolecular Pd-Catalyzed Arylation of 1-Amidosugars: A New Route to N-Glycosyl Quinolin-2-ones
Luong, Thi Thanh Huyen,Brion, Jean-Daniel,Lescop, Ewen,Alami, Mouad,Messaoudi, Samir
supporting information, p. 2126 - 2129 (2016/06/01)
The synthesis of N-glycosylated quinolin-2-ones via an intramolecular N-arylation of glycosylamides is reported. The coupling involves the use of only Pd(OAc)2 as the catalyst and nBu4NOAc as the base in 1,4-dioxane. This versatile approach allows the synthesis of various N-glycosylated quinolin-2-ones with exclusive α or β selectivity.
Cis-specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway
Emer, Enrico,Pfeifer, Lukas,Brown, John M.,Gouverneur, Veronique
supporting information, p. 4181 - 4185 (2014/05/06)
This paper describes the hydrofluorination of alkenes through sequential H- and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed. See attached PdF: A series of benzylic fluorides was prepared by hydrofluorination which proceeds through a PdII/IV catalytic manifold. The method is mechanistically distinct from previously reported radical hydrofluorination, and is characterized by its clean regioselectivity and unique cis stereospecificity. The first example of enantioselective net HF addition onto 2-vinylnaphthalene is also disclosed.