129694-51-5Relevant academic research and scientific papers
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.
The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport
Wach, Jean-Yves,Güttinger, Stephan,Kutay, Ulrike,Gademann, Karl
supporting information; experimental part, p. 2843 - 2846 (2010/07/16)
An in vivo nuclear export assay (immunostaining of Rio2 in HeLa cells) demonstrated that (R)-goniothalamin is an inhibitor of nucleocytoplasmic transport above 500 nM, which was rationalized also by molecular modeling. The cytotoxic styryl lactone natural product was prepared via an enantioselective Cr(III) catalyzed hetero Diels-Alder reaction and a Sonogashira coupling. A series of analogs was synthesized and only the oxidized goniothalamin derivative featuring an alkyne spacer was found active. Unsaturated lactones of natural origin other than leptomycin (LMB) are thus suggested to operate via a similar mechanism targeting the CRM1 nuclear receptor.
Synthesis of unsaturated lactone moieties by asymmetric hetero Diels-Alder reactions with binaphthol-titanium complexes
Quitschalle, Monika,Christmann, Mathias,Bhatt, Ulhas,Kalesse, Markus
, p. 1263 - 1265 (2007/10/03)
Natural products like ratjadone and callystatin A contain an α,β-unsaturated lactone moiety which adds to the biological activity of these compounds. Here we report a rapid and practical access to lactone precursor 3 by an asymmetric hetero Diels-Alder reaction as the key step and its subsequent transformation into a suitable building block 4.
Enantioselective Syntheses of (+)-Acetylphomalactone and (6R)-(+)-Goniothalamin from 2-Furylmethanols
Honda, Toshio,Kametani, Tetsuji,Kanai, Kazuo,Tatsuzaki, Yoko,Tsubuki, Masayoshi
, p. 1733 - 1737 (2007/10/02)
Enantioselective syntheses of two 6-substituted 5,6-dihydro-2H-pyran-2-ones, (+)-acetylphomalactone and (6R)-(+)-goniothalamin, are described which use the kinetic resolution of racemic secondary 2-furylmethanols.
