Structure of leuconolam, an alkaloid containing an unusual nine-membered ring

Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group

“…Goh and coworkers reported the isolation of 1 1 from the Leuconotis plants L. griffithii and L. eugenifolia located in Malaysia. 2 This open-ring indole is a member of the aspidosperma class of anti-mitotic alkaloids.…”

“…Some of the key structural features of 1 are revealed more explicitly by its single crystal X-ray structure. 1b In particular, the styrenyl moiety and the acetanilide functional group are non-coplanar with the benzenoid ring. Therefore, the molecule is axially chiral around the arene-alkene C14b-C14a bond.…”