57234-29-4Relevant articles and documents
Dearomative enantio- and diastereoselective difluorination of resorcinol derivatives
Egami, Hiromichi,Hamashima, Yoshitaka,Otsubo, Minami,Sakimoto, Kousuke
supporting information, (2021/08/18)
We herein report enantio- and diastereoselective fluorination of naphthoresorcinol and resorcinol derivatives for the first time using a dicarboxylate phase-transfer catalyst. Stereoselective oxidative transformation of resorcinol derivatives is considered to be difficult because of their high reactivity, multiple reaction sites, and multiple hydrogen bond interactions due to the presence of the two hydroxy groups. Even though resorcinol and its oxidized frameworks are widely found in bioactive natural compounds, dearomative asymmetric fluorination of resorcinol derivatives remains unexplored. We found that our chiral dicarboxylate phase-transfer catalyst could serve as an effective catalyst for the purpose. Interestingly, naphthoresorcinols and resorcinols were converted to difluorination products preferentially rather than monofluorinated products. It is noteworthy that asymmetric desymmetrization of symmetrically substituted resorcinols occurred with up to 95% ee and the reaction was tolerant of various functional groups.
Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities
Afonso, Carlos M. M.,Azevedo, Carlos M. G.,Bousbaa, Hassan,Ferreira, Helena,Henriques, Ana,Loureiro, Daniela R. P.,Magalh?es, álvaro F.,Neves, Nuno,Pinto, Joana,Pinto, Madalena M. M.,Reis, Salette,Soares, José X.,Vieira, Sara
supporting information, (2020/04/17)
Natural products have always been an important source of new hits and leads in drug discovery, with the marine environment being regarded as a significant source of novel and exquisite bioactive compounds. Yicathins B and C are two marine-derived xanthones that have shown antibacterial and antifungal activity. Herein, the total synthesis of these yicathins and six novel analogues is reported for the first time. As marine natural products tend to have very lipophilic scaffolds, the lipophilicity of yicathins and their analogues was evaluated in the classical octanol/water system and a biomimetic model-based system. As the xanthonic nucleus is a “privileged structure”, other biological activities were evaluated, namely antitumor and anti-inflammatory activities. An interesting anti-inflammatory activity was identified for yicathin analogues that paves the way for the design of dual activity (anti-infective and anti-inflammatory) marine-inspired xanthone derivatives.
Synthesis of bavachromanol from resorcinol via a tandem cationic cascade/EAS sequence
Shah, Parin A.,Wiemer, David F.
supporting information, p. 1363 - 1365 (2018/03/07)
The natural chalcone bavachromanol has been prepared through a tandem reaction sequence that joins cationic cyclization of an epoxide to an adjacent MOM-acetal with electrophilic aromatic substitution by a presumed methoxymethylene cation. Only a single regioisomer of the tandem product was observed, with substitution taking place exclusively ortho to the position of the original acetal. This regiocontrol provided a key intermediate from a symmetrical precursor, and allowed preparation of the meroterpenoid through a short reaction sequence.
