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Z. Naturforsch. 2014,
69b, 627 – 640
doi:10.5560/ZNB.2014-4045
Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids
Zugänge zu Isomeren und Verwandten der Lamellarin-Alkaloide
Johannes Gutenberg-Universität Mainz, Institut für Organische Chemie, Duesbergweg 10–14, 55128 Mainz, Deutschland
Reprint requests to Prof. Dr. T. Opatz. Fax: +496131-39-22338. E-mail:
opatz@uni-mainz.de
Received February 25, 2014 / published online May 7, 2014
Synthetic approaches to novel isomers and unprecedented structural relatives of the lamellarin alkaloids are reported. During our studies on methods to construct the lamellarin skeleton, we found the condensation of chroman-4-one derivatives with 1-benzyl-3,4-dihydroisoquinolines or the Pd-catalyzed cyclocarbonylation of o-halogenated precursors followed by Baeyer-Villiger oxidation to be unsuitable. Nevertheless, these routes produced interesting structural relatives of the natural alkaloids.
Key words: Alkaloids, Natural Products, Total Synthesis, Transition Metals, Carbonylation