928665-77-4Relevant academic research and scientific papers
A bio-inspired total synthesis of tetrahydrofuran lignans
Albertson, Anna K. F.,Lumb, Jean-Philip
, p. 2204 - 2208 (2015)
Lignan natural products comprise a broad spectrum of biologically active secondary metabolites. Their structural diversity belies a common biosynthesis, which involves regioand chemoselective oxidative coupling of propenyl phenols. Attempts to replicate this oxidative coupling have revealed significant challenges for controlling selectivity, and these challenges have thus far prevented the development of a unified biomimetic route to compounds of the lignan family. A practical solution is presented that hinges on oxidative ring opening of a diarylcyclobutane to intercept a putative biosynthetic intermediate. The effectiveness of this approach is demonstrated by the first total synthesis of tanegool in 4 steps starting from ferulic acid, as well as a concise synthesis of the prototypical furanolignan pinoresinol.
Preparation method and application of N-(beta-L-rhamnopyranosyl)ferulic acid amide
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Paragraph 0134-0138; 0155-0160, (2021/07/21)
The invention relates to a preparation method of a compound I N-(beta-L-rhamnopyranosyl)ferulic acid amide and application of the compound I in preparation of drugs for relieving or treating mitochondrial dysfunction and A[beta]-induced mitochondrial dysfunction in subjects, treating depression and improving or enhancing cognitive functions.
Explorations into neolignan biosynthesis: Concise total syntheses of helicterin B, helisorin, and helisterculin A from a common intermediate
Snyder, Scott A.,Kontes, Ferenc
supporting information; experimental part, p. 1745 - 1752 (2009/07/25)
Helicterins A and B (1 and 2), helisorin (3), and helisterculin A (4) are structurally unique natural products with the ability to combat the avian myeloblastosis virus. Biogenetically, their architectures are considered to be products of seemingly straightforward Diels-Alder, radical-based, or acid-induced dimerizations of common, simpler precursors. Yet, the pursuit of such blueprints in the laboratory has failed thus far in enabling their successful synthesis. Herein, we describe the first total syntheses of three of these natural products. Key features include the use of a building block distinct from Nature's likely starting material, highly complex retro Diels-Alder/Diels-Alder reaction cascades, an unconventional protecting group to achieve the proper balance of chemical reactivity on sensitive scaffolds, and several carefully developed reactionconditions that effectively balance competing reaction pathways.
