Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity

Synthesis of (−)‐Cannabimovone and Structural Reassignment of Anhydrocannabimovone through Gold(I)‐Catalyzed Cycloisomerization

“…Herein, we report the first total synthesis of enantiopure cannabimovone ( 3 ) and also revise the structure originally assigned to anhydrocannabimovone from trans ‐fused 6′ to cis ‐tetrahydro‐1 H ‐cyclopenta[ b ]benzofuran 6 . Our approach to the synthesis of these compounds relies on a gold(I)‐catalyzed cycloisomerization10, 11, 12, 13, 14, 15 of aryl‐substituted 1,5‐enyne 7 , which could be obtained in a few steps from commercially available (+)‐methyl ( S )‐3‐hydroxybutyrate ( 9 ; Scheme 2). …”

A fluorescein-based chemodosimeter for selective gold(III) ion monitoring in aqueous media and living systems

“…At the end of the reaction the crude product was extracted with dichloromethane (DCM) (3 × 10 mL), the organic layers were collected and dried over anhydrous MgSO 4 , concentrated in a vacuum, and purified by way column chromatography (DCM/MeOH = 20/1) in order to yield 95 mg of compound FL-2 (58%) as a yellow solid (Scheme 2). 1 …”

“…Given their exceptional catalytic features, gold species furthermore outshine other transition metal ion species. For these and other reasons, the number of synthetic methods using gold as a catalyst in recent studies has risen sharply [1][2][3][4][5][6]. However, products obtained by way of gold catalysis-often candidates for certain drugs and medicines-may nevertheless contain gold impurities and thus pose serious health and environmental concerns.…”

A simple Ag(I)-enyne cation

“…A plethora of gold(I) complexes and enyne substrates have been employed to access a variety of products with increased molecular complexity under very mild reaction conditions. [1][2][3][4][5][6] The mechanism is presumed to proceed via initial coordination of the gold(I) moiety to the alkyne which enhances its electrophilicity allowing for subsequent nucleophilic attack from the alkene. [7][8] However, low temperature NMR spectroscopy investigations indicated no preference between alkyne and alkene coordination, suggesting that the procedure may be kinetically rather than thermodynamically controlled.…”