Catalytic enantioselective total synthesis of (−)-ar-Tenuifolene

[Display omitted] •Asymmetric total synthesis of naturally occurring (−)-ar-tenuifolene (1) has been accomplished.•Pd(II)-Catalyzed (p-tolyl)boronic acid addition onto 3-methylcyclohex-2-enone afforded (−)-11 in 90% ee.•A highly diastereoselective MeLi addition onto (−)-11 afforded tertiary alcohol 14 in >20:1 dr.•Total synthesis reported in 3 steps with 72.8% overall yield from commercially available 16. First catalytic asymmetric total synthesis of aromatic sesquiterpene, (−)-ar-teunifolene (1) is featured (3 steps, 75% overall yields) from commercially available 3-methyl cyclohex-2-enone 16. The enantioenriched 3,3-disubstituted cyclohexanone 11 is obtained from Pd(II)-catalyzed enantioselective (p-tolyl)boronic acid addition to 3-methyl cyclohex-2-enone 16 in 90% ee, which is found to be the key intermediate. A diastereoselective methyllithium addition of this enantioenriched product followed by dehydration completes straightforward access to (−)-ar-teunifolene (1).