Methyl 12-bromodehydroabietate

Abstract

The title compound [systematic name: (1R)-methyl 6-bromo-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate], C21H29BrO2, was synthesized from N-bromosuccinimide and methyl dehydroabietate, which was prepared through an esterification reaction using dehydroabietic acid and methanol as raw materials. The three six-membered rings adopt planar (mean deviation = 0.002 Å) half-chair and chair conformations. The two cyclohexane rings form a trans ring junction with the two methyl groups in axial positions. The crystal structure is stabilized by weak intermolecular C—H...O contacts along the b axis.