Santa Maria do Suaçuí, Brazil
Santa Maria do Suaçuí, Brazil

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Schneider C.C.,Laboratorio Of Sintese | Caldeira H.,Laboratorio Of Sintese | Gay B.M.,Laboratorio Of Sintese | Back D.F.,Federal University of Santa Maria | Zeni G.,Laboratorio Of Sintese
Organic Letters | Year: 2010

(Figure Presented) The synthesis of various Z-enynols via reaction of vlnyllithlum Intermediate with aldehydes and ketones Is described. The subsequent cyclizatlon of a wide variety of Z-enynols afforded substituted furans and dihydrofurans with high regloselectlvity under mild reaction conditions. © 2010 American Chemical Society.

PubMed | Laboratorio Of Sintese
Type: Journal Article | Journal: Journal of natural products | Year: 2010

The first total syntheses of four new polyacetylene compounds have been achieved using convergent routes, which involved Cadiot--Chodkiewicz copper-catalyzed cross-coupling reactions to sp-sp centers as the key steps. 19-Furan-2-ylnonadeca-5,7-diynoic acid (1), 19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester (2), 2-pentacosa-7,9-diynylfuran (3), and 21-furan-2-ylhenicosa-14,16-diyn-1-ol (4) were stable and could be readily identified, isolated, and purified in high overall yields.

Gai R.,Laboratorio Of Sintese | Back D.F.,Federal University of Santa Maria | Zeni G.,Laboratorio Of Sintese
Journal of Organic Chemistry | Year: 2015

Herein, we report that potassium tert-butoxide-catalyzed intramolecular anionic cyclization of (2-alkynylbenzyl)oxy nitriles has been developed for the preparation of substituted benzofuroazepines. The effects of solvent, base, temperature, reaction time, and amount of base on the efficiency of cyclization reaction was investigated. The results led us to conclude that the reactions can be carried out simply by the addition of a catalytic amount of potassium tert-butoxide (20 mol %) to a solution of (2-alkynylbenzyl)oxy nitriles in tetrahydrofuran at room temperature in a short reaction time. The reaction proceeded selectively through a sequential intramolecular 5-exo-dig mode followed by a 7-endo-dig mode to give the benzofuroazepines via formation of two new carbon-carbon bonds in a one-pot procedure. © 2015 American Chemical Society.

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