Asymmetric Total Syntheses of (-)-Lycoramine, (-)-Lycoraminone, (-)-Narwedine, and (-)-Galanthamine

A concise asymmetric total synthesis of naturally occurring Amaryllidaceae alkaloids sharing dihydrobenzofuran scaffolds, (-)-galanthamine (1a), (-)-lycoramine (1b), (-)-narwedine (2a), and (-)-lycoraminone (2b), is reported. Orthoester Johnson-Claisen rearrangement of allyl alcohol (+)-9 (98% ee) in diisopropylethylamine furnished enantioenriched cyclohexene (+)-8 (97.4% ee) with a quaternary stereogenic center.

Automated summary

A concise asymmetric total synthesis method was reported for naturally occurring Amaryllidaceae alkaloids sharing dihydrobenzofuran scaffolds. Enantioenriched cyclohexene with a quaternary stereogenic center was obtained through orthoester Johnson-Claisen rearrangement of allyl alcohol.