152090-48-7Relevant articles and documents
Route to Highly Substituted Pyridines
Hilf, Justin A.,Holzwarth, Michael S.,Rychnovsky, Scott D.
, p. 10376 - 10382 (2016/11/17)
Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Hosomi-Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.
Conversion of 5-oxoalkanals to δ-lactones by an intramolecular Tishchenko reaction
Lange, Gordon L.,Organ, Michael G.
, p. 665 - 667 (2018/06/18)
Diisobutylaluminum hydride reduction of photoadducts 3 (7,8-tri- and tetrasubstituted l,3,3-trimethyl-2,4-dioxabicyclo-[4.2.0]octan-5-ones), derived from 2,2,6-trimethyl-4/f-l,3-dioxin-4-one (1), gave 6-lactones 7 in good to excellent yields if the workup involved a methanol quench followed by removal of the solvent. We propose that the reaction proceeds by an intramolecular Tishchenko reaction of the intermediate 5-oxoalkanal 5 and is catalyzed by the Lewis acid diisobutylaluminum methoxide, 8. A deuterium labelling experiment supports the mechanistic proposal and the conversion of 5-oxoalkanals other than S illustrates the scope of the procedure. To our knowledge, this is the first report of a true intramolecular Tishchenko reaction.
Fragmentation Reactions of α-Alkoxy Hydroperoxides and Application to the Synthesis of the Macrolide (+/-)-Recifeiolide
Schreiber, Stuart L.
, p. 6163 - 6165 (2007/10/02)
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