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Paper | Special issue | Vol 86, No. 2, 2012, pp.1119-1127
Published online, 24th August, 2012
DOI: 10.3987/COM-12-S(N)59
Synthesis of Calycotomine and N-Methylcalycotomine Using a Petasis Reaction — Pomeranz-Fritsch-Bobbitt Cyclization Sequence

Maria Chrzanowska, Agnieszka Grajewska, and Maria D. Rozwadowska*

*Faculty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznań, Poland


The use of aminoacetaldehyde acetals as the amine components in the one-step, three-component Petasis reaction followed by the Pomeranz-Fritsch-Bobbitt cyclization has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline alkaloids. Using this method two alkaloids, calycotomine and N-methylcalycotomine hydrochlorides, have been prepared in 61% overall yield.