The palladium-mediated cross-coupling of bromotropolones with organostannanes; application to concise syntheses of β-dolabrin, β-thujaplicin, 7-methoxy-4-isopropyltropolone, and β-thujaplicinol

Abstract

The bromotropolones (1), (2), and (3) cross-couple with organostannanes in the presence of palladium(0) to produce alkyl, alkenyl, or aryl substituted tropolones; the methodology has been applied to the synthesis of the monoterpenes β-dolabrin (4), β-thujaplicin (5), 7-methoxy-4-isopropyltropolone (7), and β-thujaplicinol (8).