The asymmetric allylation
under the assistance of catalytic amounts
of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl
hydrogen phosphate (TRIP) allows the concise construction of the lignan
scaffold from simple aldehydes and allylic bromides with full control
of the two formed stereocenters. This young methodology has been employed
to synthesize four naturally and pharmaceutically active lignans.
Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene
classes have been synthesized in 40–47% overall yield along
four-step synthetic routes.