127180-29-4Relevant academic research and scientific papers
Perylenequinone natural products: Total synthesis of hypocrellin A
O'Brien, Erin M.,Morgan, Barbara J.,Mulrooney, Carol A.,Carroll, Patrick J.,Kozlowski, Marisa C.
, p. 57 - 68 (2010)
(Chemical Equation Presented) An efficient and stereoselective total synthesis of the perylenequinone natural product hypocrellin A (1) is described. The key features include a potentially biomimetic 1,8-diketone aldol cyclization to set the centrochiral C7,C7′-stereochemistry, bis(trifluoroacetoxy)iodobenzene mediated oxygenation, a palladium-catalyzed decarboxylation, and an enantioselective catalytic oxidative 2-naphthol coupling to establish the biaryl axial chirality. The helical stereochemistry is formed from an axial chiral intermediate and is then utilized in a dynamic stereochemical transfer to dictate the stereochemistry of the C7,C7′-seven membered ring formed during the aldol cyclization.
