The synthesis of pentacyclic apogeissoschizine-type compounds is reported. It involves the construction of the seven-membered E ring by addition of the enolate derived from methyl 1- indolepropionate to the γ-position of a pyridinium salt, with subsequent acid-promoted cyclization of the resulting 1, 4-dihydropyridine, and the closure of the C ring by cyclization on the indole 3-position in the last synthetic step.
