P. Wessig, D. Badetko, M. Czarnecki, L. Wichterich, P. Schmidt, C. Brudy, E. Sperlich, A. Kelling
Studies toward the Total Synthesis of Arylnaphthalene Lignans via a\r\nPhoto-Dehydro-Diels-Alder (PDDA) Reaction
J. Org. Chem. 2022, 87, 5904-5915
DOI: 10.1021/acs.joc.2c00195
An efficient method for the preparation of arylnaphthalene lignans (ANLs) was developed, which is based on the Photo-Dehydro-DIELS-ALDER (PDDA) reaction. While intermolecular PDDA reactions turned out to be inefficient, the intramolecular variant using suberic acid as tether linking two aryl propiolic esters smoothly provided naphthalenophanes. The irradiations were performed with a previously developed annular continuous-flow reactor and UVB lamps. In this way, the natural products Alashinol D, Taiwanin C, und an unnamed ANL could be prepared.
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