ArticleJournal of the American Chemical Society2016
Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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17 citing papers in PubMed.
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- An Enantiodefined Conformationally Constrained Fatty Acid Mimetic and Potent Inhibitor of ToxT.ACS medicinal chemistry letters · 2021Article
- The search for, and chemistry and mechanism of, neurotrophic natural products.Journal of natural medicines · 2020Review
- Harpagide, a natural product, promotes synaptic vesicle release as measured by nanoelectrode amperometry.Chemical science · 2019Article
- Synthesis of C14-Desmethylene Corialactone D and Discovery of Inhibitors of Nerve Growth Factor Mediated Neurite Outgrowth.Organic letters · 2019Article
- Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.Journal of the American Chemical Society · 2019Article
- Modern applications of low-valent early transition metals in synthesis and catalysis.Nature reviews. Chemistry · 2019Article
- Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species.The Journal of organic chemistry · 2018Article
- Total synthesis of complex terpenoids employing radical cascade processes.Natural product reports · 2018Review
- Total Syntheses of (-)-Majucin and (-)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes.Journal of the American Chemical Society · 2017Article
- Synthesis of Highly Oxygenated Carbocycles by Stereoselective Coupling of Alkynes to 1,3- and 1,4-Dicarbonyl Systems.Journal of the American Chemical Society · 2017Article
- The Development of Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling Chemistry.Israel journal of chemistry · 2017Article
- Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.Journal of the American Chemical Society · 2016Article
- Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.Tetrahedron · 2016Article
- Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade.Angewandte Chemie (International ed. in English) · 2016Article
- A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.ARKIVOC : free online journal of organic chemistryArticle
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Abstract
An asymmetric approach to the synthesis of neurotrophic seco-prezizaane sesquiterpenes is described that is based on the strategic application of a hydroxyl-directed metallacycle-mediated [2 + 2 + 2] annulation and an intramolecular radical cyclization cascade. Targets prepared are among the most potent members of the natural product class and include (1R,10S)-2-oxo-3,4-dehydroneomajucin, (2S)-hydroxy-3,4-dehydroneomajucin, and (-)-jiadifenin. In addition to representing the first application of the alkoxide-directed metallacycle-mediated hydrindane-forming annulation reaction in natural product synthesis and the first total synthesis of (2S)-hydroxy-3,4-dehydroneomajucin, these pursuits have resulted in the elucidation of a complex radical cascade process for installation of the C5 quaternary center common to the natural product class.
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