64543-31-3Relevant academic research and scientific papers
Enantioselective syntheses of (R)- and (S)-argentilactone and their cytotoxic activities against cancer cell lines
De Fatima, ?ngelo,Kohn, Luciana Konecny,Ant?nio, Márcia Aparecida,De Carvalho, Jo?o Ernesto,Pilli, Ronaldo Aloise
, p. 5437 - 5442 (2004)
Concise total syntheses of (R)- and (S)-argentilactone have been developed via enantioselective catalytic allylation (ECA) and ring-closing metathesis pathways. Both enantiomers were obtained in four steps and 39% overall yield and 82-84% ee from 2-octynal. In addition, we present the results of in vitro activity of (R)- and (S)-argentilactone against cancer cell line. Concise total syntheses of (R)- and (S)-argentilactone have been developed via enantioselective catalytic allylation (ECA) and ring-closing metathesis pathways (four steps, 39% overall yield and 82-84% ee) from 2-octynal and their in vitro activity against cancer cells is described.
Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
, p. 4433 - 4439 (2021/08/20)
α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
Asymmetric total syntheses of (R)-(-)-argentilactone and (S)-5-hexadecanolide
Sabitha, Gowravaram,Fatima, Narjis,Swapna,Yadav
, p. 2879 - 2884 (2008/02/05)
The simple and efficient asymmetric syntheses of (R)-(-)-argentilactone and (S)-5-hexadecanolide were achieved from the same starting material by a similar strategy. The key intermediates for both molecules were chiral 5-hydroxyalk-2-en-6-ynoates. Georg T
Total syntheses of (R)-argentilactone and (R)-goniothalamin via catalytic enantioselective allylation of aldehydes
De Fátima, ?ngelo,Pilli, Ronaldo Aloise
, p. 8721 - 8724 (2007/10/03)
The total syntheses of (R)-argentilactone (five steps, 25% overall yield) and (R)-goniothalamin (three steps, 61% overall yield) have been described through the enantioselective catalytic allylation of aldehydes (including a propargylic aldehyde) which provided a rapid access to these natural products that display very interesting biological activities.
Synthesis of (R)-(-)-argentilactone
Hansen, Trond Vidar
, p. 547 - 550 (2007/10/03)
A synthesis of (R)-(-)-argentilactone is reported starting from the (S)-enantiomer of glycidol. The synthesis is based on ring closing metathesis of the acrylic ester of (R)-1-O-(tert-butyldiphenylsilyl)-4-penten-1,2-diol 4.
Total synthesis and anti-leishmanial activity of R-(-)-argentilactone
Saeed, Muhammad,Ilg, Thomas,Schick, Miriam,Abbas, Muhammad,Voelter, Wolfgang
, p. 7401 - 7403 (2007/10/03)
Starting from the commercially available D-glucal (2), the naturally occurring α,β-unsaturated δ-lactone argentilactone (1a) has been synthesized. The important step is the configuration inversion at C-6 by the Mitsunobu reaction following the sugar-non-sugar-sugar strategy. The synthetic argentilactone has been tested against Leishmania mexicana for bioactivity.
An efficient enantioselective synthesis of argentilactone
Brown, H. C.,Wetherill, R. B.
, p. 739 - 742 (2007/10/03)
Asymmetric allylboration of 2'-octynal with (+)-B-allyldiisopinocampheylborane provides the corresponding homoallylic alcohol in 80 percent yield. The alkynenol is stereoselectively hydrogenated in the presence of Lindlar catalyst, converted to the corresponding acrylic acid, and cyclized by refluxing in dichloromethane in the presence of 10 mol percent of Grubbs' catalyst to provide the natural enantiomer of (R)-(-)-argentilactone in 44 percent overall yield.
ENANTIOSELECTIVE SYNTHESIS OF 6-SUBSTITUTED 5,6-DIHYDRO-α-PYRANONES, (+)-GONIOTHALAMIN AND (-)-ARGENTILACTONE
Tsubuki, Masayoshi,Kanai, Kazuo,Honda, Toshio
, p. 281 - 288 (2007/10/02)
An enantioselective synthesis of (+)-goniothalamin and (-)-argentilactone has been accomplished by employing the Wittig reactions of phosphoranes with the aldehyde (12) generated in situ by Swern oxidation of the alcohol (13) as a key step.
A PRACTICAL ROUTE TOWARDS α,β-UNSATURATED δ-LACTONES BASED ON A STRATEGY. SYNTHESIS OF (-)-ARGENTILACTONE
Carretero, Juan Carlos,Ghosez, Leon
, p. 2059 - 2062 (2007/10/02)
The lithio derivative of methyl 3-phenylsulphonylorthopropionate 1 reacts with epoxides to give, after acidic work-up and treatment with p-toluenesulphonic acid, β-phenylsulphonyl δ-lactones 2.These are directly converted into the corresponding α,β-unsaturated δ-lactones 3 upon treatment with triethylamine or DBU.An application of this new method to the synthesis of (-)-argentilactone 4 is described.
SYNTHESES OF ARGENTILACTONE 11 AND GONIOTHALAMIN 15
O'Connor, Brian,Just, George
, p. 5201 - 5202 (2007/10/02)
Syntheses of (-)-(5R)-argentilactone 11 and (+)-(5R)-goniothalamin 15 are described starting from olefin 4.
