117828-42-9Relevant academic research and scientific papers
Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors
Zhang, Wenhan,Chu, Jennifer,Cyr, Andrew M.,Yueh, Han,Brown, Lauren E.,Wang, Tony T.,Pelletier, Jerry,Porco, John A.
, p. 12891 - 12900 (2019/09/09)
Rocaglates are a family of natural products isolated from the genus Aglaia which possess a highly substituted cyclopenta[b]benzofuran skeleton and inhibit cap-dependent protein synthesis. Rocaglates are attractive compounds due to their potential for inhibiting tumor cell maintenance in vivo by specifically targeting eukaryotic initiation factor 4A (eIF4A) and interfering with recruitment of ribosomes to mRNA. In this paper, we describe an intercepted retro-Nazarov reaction utilizing intramolecular tosyl migration to generate a reactive oxyallyl cation on the rocaglate skeleton. Trapping of the oxyallyl cation with a diverse range of nucleophiles has been used to generate over 50 novel amidino-rocaglate (ADR) and amino-rocaglate derivatives. Subsequently, these derivatives were evaluated for their ability to inhibit cap-dependent protein synthesis where they were found to outperform previous lead compounds including the rocaglate hydroxamate CR-1-31-B.
Total synthesis and biological activity of (±)-rocaglamide and its 2,3-di-epi analogue
Li, Hongsen,Fu,Wang,Li,Liu,Xie,Ma,Qin, Zhaohai
experimental part, p. 1753 - 1758 (2009/04/07)
By introducing the strategy of intramolecular reductive coupling to construct the cyclopenta[b]benzofuran skeleton, the shortest and most efficient synthetic method hitherto was now established to rocaglamide 1 and its 2,3-di-epi analogue 3 in racemic form by Michael addition, SmI 2-promoted intramolecular keto-ester coupling, amination of the ester intermediate, and reduction of carbonyl with Me4NBH(OAc) 3. Several steps were highly stereoselective or even stereospecific. The bioassay results indicated that both 1 and 3 were much better repellents against Plutella xylostella than azadirachtin; the insecticidal activity of 1 was higher than that of azadirachtin against Pieris rapae, P. xylostella, Laphygma exigua, and Helicoverpa armigera, but that of 3 was lower. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Total synthesis of (±)-rocaglamide and some aryl analogues
Dobler, Markus R,Bruce, Ian,Cederbaum, Fredrik,Cooke, Nigel G,Diorazio, Louis J,Hall, Roger G,Irving, Ed
, p. 8281 - 8284 (2007/10/03)
The insecticidal activity found for rocaglamide and its congeners, prompted us to establish a short and efficient synthesis of the natural product and some synthetic 'halo-aryl' analogues. Pd-catalysed cross-coupling reactions of the bromo analogue were then explored in order to gain a suitable access to a broad range of unnatural analogues. The key step of our approach is a keto-aldehyde acyloin ring-closure followed by a Stiles carboxylation.
Synthesis of the Novel Anti-leukaemic Tetrahydrocyclopentabenzofuran, Rocaglamide and Related Synthetic Studies
Davey, Andrew E.,Schaeffer, Marcel J.,Taylor, Richard J. K.
, p. 2657 - 2666 (2007/10/02)
Two approaches to the rocaglamide tricyclic skeleton are described.The first, which employs an unusual dithianyl anion to carbonyl addition reaction, provides access to α-phenyl rocaglamide analogues.The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both α- and β-phenyl substituents.A total synthesis of rocaglamide, in racemic form, is described using this second approach.The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield > 6percent.The synthesis of 1-epi-rocaglamide 29b is also described.
A Synthetic Approach to Rocaglamide via Reductive Cyclization of δ-Keto Nitriles
Kraus, George A.,Sy, James O.
, p. 77 - 83 (2007/10/02)
The anticancer agent rocaglamide contains a novel bicyclooctanol structure.The approach to this molecule involved the preparation of a hydroxy ketone intermediate via a samarium-mediated cyclization.This ketone was then converted into an excellent
