117828-33-8Relevant academic research and scientific papers
Total synthesis of (±)-rocaglamide via oxidation-initiated nazarov cyclization
Malona, John A.,Cariou, Kevin,Spencer, William T.,Frontier, Alison J.
, p. 1891 - 1908 (2012/04/23)
This article describes the evolution of a Nazarov cyclization-based synthetic strategy targeting the anticancer, antiinflammatory, and insecticidal natural product (±)-rocaglamide. Initial pursuit of a polarized heteroaromatic Nazarov cyclization to construct the congested cyclopentane core revealed an unanticipated electronic bias in the pentadienyl cation. This reactivity was harnessed in a successful second-generation approach using an oxidation-initiated Nazarov cyclization of a heteroaryl alkoxyallene. Full details of these two approaches are given, as well as the characterization of undesired reaction pathways available to the Nazarov cyclization product. A sequence of experiments that led to an understanding of the unexpected reactivity of this key intermediate is described, which culminated in the successful total synthesis of (+)-rocaglamide.
A highly efficient synthesis of rocaglaols by a novel α-arylation of ketones
Diedrichs, Nicole,Ragot, Jacques P.,Thede, Kai
, p. 1731 - 1735 (2007/10/03)
Rocaglaols are natural products exhibiting a range of biological activities. A new synthetic method for the α-arylation of ketones allows for the synthesis of previously inaccessible rocaglaol derivatives. The key sequence consists of a previously unreported Suzuki type reaction using brominated si-lyl enol ethers as substrates followed by deprotection of the arylated silyl enol ethers. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Palladium catalysed arylation of 6,8-dimethoxybenzofuranone
Souna Sido, Abdelkarim Sani,Boulenger, Lo?c,Désaubry, Laurent
, p. 8017 - 8018 (2007/10/03)
6,8-Dimethoxybenzofuranone was arylated in the presence of a palladacycle catalyst and p-methoxyphenol to afford precursors of anti-cancer and anti-inflammatory drugs.
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.
