Catalytic asymmetric total syntheses of sesquiterpenoids, (+)- and (−)-ar-macrocarpene
2020
Khatua, Arindam | Roy, Avishek | Bisai, Vishnumaya
Concise catalytic asymmetric total syntheses of aromatic sesquiterpenes, naturally occurring (+)-ar-macrocarpene (1) and unnatural (−)-ar-macrocarpene (ent-1) have been featured (6 steps, ∼60–61% overall yields) from commercially available 4,4-dimethylcyclohex-2-enone 16. The enantioenriched allyl alcohol 12 is obtained from catalytic enantioselective reduction of enone 13b using Corey-Bakshi-Shibata catalyst in 93% ee, which is found to be the key intermediate. A highly diastereoselective hydrogenation of enantioenriched allyl alcohol 12 (10.3:1 dr) followed by deoxygenation completes straightforward access to (+)-ar-macrocarpene (1) and (−)-ar-macrocarpene (ent-1).
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