Total Synthesis of (+)-Galbulin and Unnatural Lignans

Abstract

The total synthesis of (+)-galbulin was achieved in 15% yield and 99% ee over eight steps from commercially available 4-veratraldehyde. The key steps include Meyer's asymmetric tandem addition to a chiral 2-oxazoline-substituted naphthalene, a Pd-catalyzed stereospecific decarboxylative γ-arylation, and a formal anti-Markovnikov hydromethylation. In addition, five unnatural lignans were synthesized using the same synthetic strategy.