Synthesis of the Lycopodium Alkaloid (+)-Lycoflexine

Ramharter, Jürgen; Weinstabl, Harald; Mulzer, Johann

Journal of the American Chemical Society  (2010),  132(41),  14338-14339

The first total synthesis of (+)-lycoflexine (1), a constituent of Lycopodium clavatum var. inflexum, has been accomplished in eight steps with 13% overall yield. Our synthesis covers four one-pot reactions, including a tandem Sakurai/aldol sequence, a novel hydroboration/oxidation procedure, a deprotection/transannular Mannich reaction, and as a highlight, a tandem catalysis cascade combining an enynene ring-closing metathesis and a selective hydrogenation.