1159706-94-1Relevant articles and documents
Pd-Catalyzed Enantioselective Dearomative Allylic Annulation to Access PPAPs Analogues
Li, Sanliang,Chen, Qiaoyu,Xie, Xiaoxiao,Yang, Junfeng,Zhang, Junliang
, p. 7824 - 7828 (2021/10/20)
Polycyclic polyprenylated acylphloroglucinols (PPAPs) share a common bicyclo[3.3.1]alkenone core structure and attract numerous attention from synthetic organic chemists due to their fascinating biological properties and associated synthetic challenges. We present herein that Pd-phosphoramidite catalysts promote the enantioselective dearomative allylic annulation reaction between allyl desoxyhumulones and allylic dicarbonates, affording PPAPs analogues in good yields and enantioselectivities. The reaction likely proceeds through two-step dearomative allylation by Pd, and the C-allylation pathway is the dominant mechanistic model.
Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization
Boyce, Jonathan H.,Porco, John A.
supporting information, p. 7832 - 7837 (2014/08/05)
We report a stereodivergent, asymmetric total synthesis of (-)-clusianone in six steps from commercial materials. We implement a challenging cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms. Mechanistic studies point to the unique ability of formic acid to mediate the cyclization forming the clusianone framework. Aim for selectivity: (-)-Clusianone was produced by a stereodivergent asymmetric total synthesis in six steps from commercial materials. The synthesis utilizes a challenging formic acid-mediated cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms.
Manganese(III)-mediated transformations of phloroglucinols: A formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones
Mitasev, Branko,Porco Jr., John A.
supporting information; experimental part, p. 2285 - 2288 (2009/11/30)
Manganese(III)-mediated oxidative transformations of dearomatized phloroglucinol (1,3,5-trihydroxybenzene) derivatives are reported. A number of cyclization modes have been observed, including polycyclization to afford bicyclo[2.2.2]octadiones via a forma