78589-63-6Relevant academic research and scientific papers
Studies toward the Total Synthesis of Arylnaphthalene Lignans via a Photo-Dehydro-Diels-Alder (PDDA) Reaction
Wessig, Pablo,Badetko, Dominik,Czarnecki, MacIej,Wichterich, Lukas,Schmidt, Peter,Brudy, Cosima,Sperlich, Eric,Kelling, Alexandra
, p. 5904 - 5915 (2022/04/22)
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, and an unnamed ANL could be prepared.
NOUVEAU MODE DE CYCLYSATION DE CETO-YLURES. APPLICATION A UNE SYNTHESE IGINALE D'ACYL-3 HYDROXY-4-COUMARINES ET DE L'HYDROXY-11 BENZO-(b) 12 XANTHONE-12
Babin, P.,Dunogues, J.,Petraud, M.
, p. 1131 - 1139 (2007/10/02)
The thermal decomposition of keto-ylides resulting from the reaction of m- and p-acetoxy benzoyl chlorides with Ph3P=CH-COOMe leads, after saponification to m- and p-phenylpropiolic acid respectively.Ortho substitution by an acyl group generally changes the orientation of the reaction.Thus o-acetoxy-, benzoyloxy- or phenylacetoxy benzoyl chlorides respectively afford: and (R=Me,Ph) in satisfactory yields.Saponification of the first and second ones gives: (R=Me, Ph).This constitutes a new, convenient route to 3-acyl 4-hydroxy cumarins and 11-hydroxy 12H-benzoxanthene 12-one.Formation of these last products involves the carbonyl of the acyloxy-substituent and not of the acyl chloride as previously observed in these series.
