A highly stereoselective intramolecular Diels–Alder reaction for construction of the AB ring moiety of bruceantin. Issue 10 (4th March 2015) - Usui, Kenji
Graphical abstract: Abstract: A highly stereoselective intramolecular Diels–Alder (IMDA) reaction for the construction of the AB ring moiety of bruceantin is described. The product of the IMDA reaction comprises a trans-AB ring junction and stereotetrad including an all carbon quaternary stereogenic center, wherein three stereogenic centers correspond to those of bruceantin. Functional groups embedded in the product are suitable for a variety of transformations. Hence, this IMDA product could be a useful intermediate for the enantioselective total synthesis of not only bruceantin, but also other bioactive compounds.