Replacement of the central, para-substituted fluorophenyl ring in the γ-secretase inhibitor 1 (BMS-708,163) with the bicyclo[1.1.1]pentane motif led to the discovery of compound 3, an equipotent enzyme inhibitor with significant improvements in passive permeability and aqueous solubility. The modified biopharmaceutical properties of 3 translated into excellent oral absorption characteristics (~...

Microwave assisted Diels-Alder cycloaddition of 5-Br-N-benzylpyridinone (2) with methyl acrylate is described to gain an easy access to 7-bromo-2-benzyl-3-oxo-2-aza-5 or 6-carbomethoxy bicyclo[2.2.2]oct-7-enes (3)-(6). The preparation of the ibogaine analogue 20-desethyl-(20-endo)-hydroxymethyl-11-demethoxyibogaine (17) is described by stereoselective hydrogenation of the C(7)-C(8) double bond....

We report a two-step approach to obtain synthetically versatile bicyclo[1.1.1]pentane (BCP) derivatives using Grignard reagents. This method allows the incorporation of BCP units in tetrapyrrolic macrocycles and synthesis new class calix[4]pyrrole analogues by replacing two bridging methylene groups with units. In addition, doubly N-confused system was also formed presence electron-withdrawing ...

Massarinolin A und Purpurolide sind bioaktive Bergamotan-Sesquiterpene mit einem komplexen tetrazyklischen Grundgerüst. In der Zuschrift auf S. 25032 berichten Mingji Dai Mitarbeiter über einen divergenten enantioselektiven Ansatz für die ersten Totalsynthesen von fünf tetracyclischen Bergamotan-Sesquiterpenen, außerdem zu einer Strukturrevision führte. Der beinhaltet eine photochemische Wolff-...

Abstract An efficient protocol for the synthesis of 3‐ethynyl‐2‐aryl‐bicyclo[3.1.0]hexenes through a gold‐catalyzed enyne cyclization was established in this work. Depending on specific substitution pattern, unusual cationic rearrangements corresponding gold carbene were revealed, leading to either cyclohexadienes or 5,9‐methanobenzo[8]annulene derivatives, respectively.