Synthesis of polycyclic alkaloid-type compounds by an N -acyliminium Pictet-Spengler/diels-alder sequence
- Ruijter, Eelco
- Garcia-Hartjes, Jaime
- Hoffmann, Frank
- Vanwandelen, Loek T.M.
- Dekanter, Frans J.J.
- Janssen, Elwin
- Orru, Romano V.A.
DOIAbstract
A range of structurally diverse penta- and hexacyclic alkaloid-type compounds have been prepared in a two-step procedure from readily available starting materials. A flexible N-acyliminium Pictet-Spengler reaction employing electron-rich -arylethyl-amines, cinnamaldehyde derivatives, and alkynoyl chlorides sets the stage for an intramolecular Diels-Alder cycloaddition. The complex and diverse polycyclic alkaloid-like compounds are easily obtained in reasonable to excellent yield in a reliable and efficient reaction sequence. © Georg Thieme Verlag Stuttgart New York
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