91555-33-8Relevant academic research and scientific papers
Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N and structural reassignment of (-)-viminalin M
Dethe, Dattatraya H.,Nirpal, Appasaheb K.
, p. 7507 - 7516 (2019)
Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N, isolated from the Myrtaceae family, were accomplished in a convergent fashion in 5, 5, 1, 1, and 3 steps, respectively. A highly regio- and diastereoselective oxidative [3 + 2] cycloaddition reaction of acylphloroglucinols with α-phellandrene, diastereoselective modified Friedel-Crafts reaction of acylphloroglucinols with piperetol, and stereoselective epoxidation of extremely hindered β-face were described as key reactions.
Pd-Catalyzed Enantioselective Dearomative Allylic Annulation to Access PPAPs Analogues
Li, Sanliang,Chen, Qiaoyu,Xie, Xiaoxiao,Yang, Junfeng,Zhang, Junliang
supporting information, 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.
Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
supporting information, p. 11799 - 11804 (2014/10/16)
Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
