1198605-75-2Relevant academic research and scientific papers
Perylenequinone natural products: Evolution of the total synthesis of cercosporin
Morgan, Barbara J.,Mulrooney, Carol A.,Kozlowski, Marisa C.
supporting information; experimental part, p. 44 - 56 (2010/04/24)
(Chemical Equation Presented) The evolution of the first total synthesis of perylenequinone cercosporin is described. The key features developed during these efforts include a biscuprate epoxide alkylation, installation of the methylidene acetal, palladium-catalyzed O-arylation, and C3,C3′- decarbonylation. Due to the rapid atropisomerization of the helical axis of cercosporin (at 37°C), the sequencing of these transformations was critical. To this end, the developed protocol enabled the formation of a key advanced intermediate on preparative scale absent any atropisomerization. Furthermore, the O-arylation proved to be general, and the strategy was used in an improved synthesis of a helical chiral perylenequinone structure.
