Derivatization of sumanenetrione through Lewis acid-mediated Suzuki–Miyaura coupling and an unprecedented ring opening

Abstract

A series of sumanenetrione derivatives were synthesized through Lewis acid-mediated Suzuki–Miyaura cross-coupling. Their optical properties reflected the significantly strong electron-accepting ability of sumanenetrione. The bowl strain of 2-hydroxyphenyl derivative brought...

Strain-induced carbon–carbon bond cleavage of bowl-shaped sumanenone

“…Our group has reported osmylation to aromatic ring in sumanene 13 and the mild C–C bond cleavage of 2-hydroxyphenyl sumanenetrione. 22 In the latter case, the presence of the 2-hydroxyphenyl group is essential for the reaction to proceed. Herein, we report the Brønsted acid-mediated five-membered ring-opening of sumanenone ( 1 ) via C–C bond cleavage (Fig.…”