50667-94-2Relevant academic research and scientific papers
Palladium-Catalyzed Chemoselective Protodecarboxylation of Polyenoic Acids
Al-Huniti, Mohammed H.,Perez, Mark A.,Garr, Matthew K.,Croatt, Mitchell P.
supporting information, p. 7375 - 7379 (2019/01/03)
Conditions for the first palladium-catalyzed chemoselective protodecarboxylation of polyenoic acids to give the desired polyenes in good yields are presented. The reactions proceed under mild conditions using either a Pd(0) or Pd(II) catalyst and tolerate a variety of aryl and aliphatic substitutions. Unique aspects of the reaction include the requirement of phosphines, water, and a polyene adjacent to the carboxylic acid.
One-flask tethered ring closing metathesis-electrocyclic ring opening for the highly stereoselective synthesis of conjugated Z/E-dienes
Schmidt, Bernd,Kunz, Oliver
, p. 1008 - 1018 (2012/03/27)
A one-flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base-mediated ring opening gives 2Z,4E-configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised. Ring closing metathesis (RCM) of butenoates derived from allylic alcohols can be combined with base-induced ring opening in a one-flask sequence. In this way, dienoic acids become accessible in an operationally simple procedure in very high yields and excellent stereoselectivities, with the tether remaining in the product as a valuable functional group for further transformations. Copyright
