Studies toward the total synthesis of arylnaphthalene lignans via a Photo-Dehydro-Diels-Alder (PDDA) reaction

  • An efficient method for the preparation of arylnaphthalene lignans (ANLs) was developed, which is based on thePhoto-Dehydro-DIELS-ALDER(PDDA) reaction. While intermolecular PDDA reactions turned out to be inefficient, theintramolecular variant using suberic acid as tether linking two aryl propiolic esters smoothly provided naphthalenophanes. Theirradiations were performed with a previously developed annular continuous-flow reactor and UVB lamps. In this way, the naturalproducts Alashinol D, Taiwanin C, and an unnamed ANL could be prepared.

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Author details:Pablo WessigORCiDGND, Dominik Badetko, Maciej CzarneckiORCiDGND, Lukas Wichterich, Peter Schmidt, Cosima Brudy, Eric SperlichORCiDGND, Alexandra Kelling
Pubmed ID:
Title of parent work (English):The journal of organic chemistry
Publisher:American Chemical Society
Place of publishing:Washington
Publication type:Article
Date of first publication:2022/04/07
Publication year:2022
Release date:2023/01/23
Number of pages:12
First page:5904
Last Page:5915
Funding institution:Deutsche Forschungsgemeinschaft [We1850-12/1]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
6 Technik, Medizin, angewandte Wissenschaften / 61 Medizin und Gesundheit / 610 Medizin und Gesundheit
Peer review:Referiert
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