Abstract

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.

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