1417801-89-8Relevant academic research and scientific papers
Enantioselective and regioselective pyrone Diels-Alder reactions of vinyl sulfones: Total synthesis of (+)-cavicularin
Zhao, Peng,Beaudry, Christopher M.
, p. 10500 - 10503 (2014)
The total synthesis of (+)-cavicularin is described. The synthesis features an enantio- and regioselective pyrone Diels-Alder reaction of a vinyl sulfone to construct the cyclophane architecture of the natural product. The Diels-Alder substrate was prepared by a regioselective one-pot three-component Suzuki reaction of a non-symmetric dibromoarene. The total synthesis of (+)-cavicularin features an enantio- and regioselective Diels-Alder reaction of a pyrone with a vinyl sulfone. The substrate for this transformation is prepared by a regioselective one-pot three-component Suzuki reaction of a non-symmetric dibromoarene.
Total synthesis of (±)-cavicularin: Control of pyrone diels-alder regiochemistry using isomeric vinyl sulfones
Zhao, Peng,Beaudry, Christopher M.
, p. 402 - 405 (2013/03/13)
An intramolecular pyrone Diels-Alder reaction-elimination retro-Diels-Alder cascade of a vinyl sulfone was used in the synthesis of cavicularin, a molecule possessing conformational chirality. The vinyl sulfone substitution pattern allowed for regiocontrol in the Diels-Alder cascade event.
