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The Norrish-Yang reaction, as a typical example, demonstrates the inherent ability of photochemical reaction to facilitate formation of sterically congested C-C bonds, efficiently crafting intricate ring structure in complex organic molecules. Herein we report for the first time a unified synthesis using quinone-based acid-promoted Norrish-Yang photocyclization for the stereoselective construction of multiple avarane-type meroterpenoid natural products.
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http://dx.doi.org/10.1002/anie.202415249 | DOI Listing |
J Org Chem
August 2025
Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan.
Norrish-Yang cyclization reactions have attracted much attention in synthetic organic chemistry due to their ability to activate and functionalize inactive CH positions. In this study, we report that the diastereoselective course of the Norrish-Yang reaction of imidazolidinone derivatives is reversed by the addition of tetrabutylammonium salts (TBAX). H NMR experiments suggested that cation-π interactions between TBA and the substrate control the reactive conformation of this latter species.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
March 2025
State Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan, Key Laboratory of Natural Medicinal Chemistry Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
Plant sesterterpenoids are an extremely rare family of natural products that generally possess novel chemical structures and diverse biological activities. Herein, we report the discovery of an unprecedented group of minor plant sesterterpenoids, gracilisoids B-E (2-5), which feature two types of highly functionalized bicyclo[3.2.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
State Key Laboratory of Chemical Oncogenomics and Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology Peking University Shenzhen Graduate School, Shenzhen, 518055, P. R. China.
The Norrish-Yang reaction, as a typical example, demonstrates the inherent ability of photochemical reaction to facilitate formation of sterically congested C-C bonds, efficiently crafting intricate ring structure in complex organic molecules. Herein we report for the first time a unified synthesis using quinone-based acid-promoted Norrish-Yang photocyclization for the stereoselective construction of multiple avarane-type meroterpenoid natural products.
View Article and Find Full Text PDFOrg Lett
October 2024
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
A Norrish-Yang photocyclization reaction has been applied to regio- and stereoselective construction of the ABCDE pentacyclic motif of natural product phainanoids. The observed substrate conformation control implicates this powerful reaction could be applied to the construction of structurally diverse natural product scaffolds.
View Article and Find Full Text PDFBeilstein J Org Chem
July 2024
Department Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, 55128 Mainz, Germany.
α-Aminoacetophenones are identified as promising building blocks for the synthesis of highly substituted dioxolanes. The presented strategy is founded on the build and release of molecular strain and achieves a formal transposition of a methyl group. During light irradiation, 3-phenylazetidinols are forged as reaction intermediates, which readily undergo ring opening upon the addition of electron-deficient ketones or boronic acids.
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