Synthesis of the racemic forms of carbon–carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

“…No reaction was observed in the absence of a ligand (entry 1). The ligands ( Figure 1) were then screened while Cu 2 O and KI were used as the catalyst and iodine source, respectively (entries [14][15][16][17][18][19][20]. Only trace amounts of the desired product, (E)-β-iodo-4-methylstyrene (2b), was observed when the ligand pyridine (L2) was examined (entry 14).…”

“…When the ligands N 1 ,N 1 ,N 2 ,N 2 -tetramethylethane-1,2-diamine (L3) and pyridine-2,6-dicarboxylic acid (L4) were examined, the desired product 2b was obtained in 20% and 19% yield, respectively (entries 15 and 16). Iodide 2b was obtained in 72-87% yield when ethane-1,2-diamine (L5), L-proline (L6), 2,2-bipyridine (L7), and 1,10-phenanthroline (L8) were used as ligands (entries [17][18][19][20]. Among the ligands examined, L6 proved to be the most effective (entry 18, 87% yield).…”

Concise and Gram-Scale Total Synthesis of Lansiumamides A and B and Alatamide

“…The combined organic fractions were washed with brine and dried with anhydrous Na 2 SO 4 . The solvents were evaporated under reduced pressure and the resulting residue was purified by flash chromatography on silica gel using eluents (petroleum ether) to give the desired ( Z )-(2-iodovinyl)benzene (4) [23,24] (1.31 g, 58% yield) as a colorless oil. 1 H NMR (400 MHz, CDCl 3 ) δ: δ = 7.66–7.63 (m, 2 H), 7.43–7.36 (m, 3H), 7.33 (d, J = 8.8 Hz, 1H), 6.58 (d, J = 8.8 Hz, 1H).…”

Synthesis and biological evaluation of novel cyclopropyl derivatives as subtype-selective ligands for estrogen receptor

“…Previously, we showed the compounds with a conjugated diphenylethene skeleton, such as 2‐phenylbenzofuran derivatives, had a high ER binding affinity and subtype‐selective activity . Cyclopropyl group is a common pharmacophore in many biologically active molecules, and more importantly, this group is considered as an ethylene bioisostere . Many cyclopropyl derivatives were designed and synthesized as ligands for ERs.…”

“…[15] Cyclopropyl group is a common pharmacophore in many biologically active molecules, [16] and more importantly, this group is considered as an ethylene bioisostere. [17,18] Many cyclopropyl derivatives were designed and synthesized as ligands for ERs. For example, by converting the alkene bond of TAM to cyclopropane, a cyclopropyl derivative ( Figure 1a) of TAM was synthesized.…”