Stereoselective synthesis of (3-aminodecahydro-1,4-methanonaphthalen-2-yl)methanols targeted to the C1 domain of protein kinase C

Design and synthesis ofC3-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

“…The synthesis of propellane-bearing C 3 -symmetric derivatives starts with commercially available dicyclopentadiene and maleic anhydride ( 7 ). Here, we used a DA reaction of freshly cracked cyclopentadiene ( 6 ) and maleic anhydride ( 7 ) to obtain the endo -DA adduct 8 [ 42 ] in 98% yield. Next, this cycloadduct 8 was treated with commercially available 4-aminoacetophenone ( 9 ) in the presence of triethylamine (Et 3 N) in toluene at 140 °C to obtain the acetophenone derivative 10 in excellent yield (92%) [ 43 ].…”

Euphohelioscopin A Is a PKC Activator Capable of Inducing Macrophage Differentiation

“…This revived the interest in finding molecules able to activate PKC with distinct activities and specificities. More recently, as structural details emerged on the mechanism of PKC activation, several attempts to rationally design PKC activating or inhibiting ligands have been described (Baba et al, 2004; Boije af Gennas et al, 2009; Keck et al, 2010; Kiriazis et al, 2011). In this report we introduce a new scaffold to explore in this context: a lathyrane diterpene.…”

Copper Selective Polymeric Extractant Synthesized by Ring-Opening Metathesis Polymerization

“…Starting from the known norbornyl anhydride 1, the primary amine 2 was prepared in 89% yield via condensation with 1,6-diaminohexane in acetic acid. 25 Intermediate 2 was then condensed with dimethylpyridine-2,6dicarboxylate using catalytic acid to give the amide-ester 3 in 91% yield. Base hydrolysis of this compound using lithium hydroxide followed by acidic aqueous workup gave the free acid 4 in 89% yield.…”

“…The synthesis of a norbornyl-functionalized picolinic acid 4 suitable for preparing a ROMP-based polymer is outlined in Scheme . Starting from the known norbornyl anhydride 1 , the primary amine 2 was prepared in 89% yield via condensation with 1,6-diaminohexane in acetic acid . Intermediate 2 was then condensed with dimethylpyridine-2,6-dicarboxylate using catalytic acid to give the amide-ester 3 in 91% yield.…”