1.
Asymmetric Total Syntheses of (-)-Lycoramine, (-)-Lycoraminone, (-)-Narwedine, and (-)-Galanthamine.
J Org Chem
; 87(12): 7786-7797, 2022 06 17.
Artigo
em Inglês
| MEDLINE
| ID: mdl-35613361
RESUMO
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.