Construction of the pentacyclic ring system of apogeissoschizine
ML Bennasar, E Zulaica, BA Sufi, J Bosch
Index: Bennasar, M.-Lluisa; Zulaica, Ester; Sufi, Bilal A.; Bosch, Joan Tetrahedron, 1996 , vol. 52, # 25 p. 8601 - 8610
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Citation Number: 18
Abstract
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.
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