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Synthesis of the Pyrrole-Imidazole Alkaloid Sventrin from the Marine Sponge Agelas sventres Gregor Breckle, Kurt Polborn, and Thomas Lindel

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Synthesis of the Pyrrole-Imidazole Alkaloid Sventrin from the Marine Sponge Agelas sventres

Gregor Breckle, Kurt Polborn, and Thomas Lindel

Ludwig-Maximilians-Universität München, Department of Chemistry, Butenandtstr. 5Ð13, D-81377 Munich, Germany

Reprint requests to Prof. Dr. Th. Lindel. Fax int: +(0)89/21 80-7-77 34.

E-mail: thomas.lindel@cup.uni-muenchen.de

Z. Naturforsch.58b,451Ð456 2003; received February 17, 2003

The marine pyrrole-imidazole alkaloid sventrin (1) and the hitherto unknown dehydrooroi- din (3) have been synthesized stereoselectivelyviaalkyne intermediates. The pathways start from a 2-azido-4-alkynylimidazole which can be chemo- and stereoselectively reduced to the corresponding amino alkene using NaAlH2(OCH2CH2OMe)2(Red-Al) or, alternatively, to the amino alkyne. Selective removal of simultaneously present Boc or trityl protecting groups was possible employing eitherp-TsOH or aceticresp.formic acid.

Key words:Alkynes, Red-Al, Marine Natural Products

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