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Palladium Catalyzed Synthesis of the Furanoterpene Ircinin-4

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Gastner,  Thomas
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Rust,  Jörg
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Gastner, T., & Rust, J. (1999). Palladium Catalyzed Synthesis of the Furanoterpene Ircinin-4. Synlett, (1), 95-96. doi:10.1055/s-1999-2534.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-21FC-5
Abstract
A flexible entry into 2,4-disubstituted furan derivatives is outlined employing sulfonium salt 1 as a well accessible starting material. Condensation of the sulfur ylide derived from 1 with alde-hydes, palladium catalyzed opening of the vinyloxirane thus formed, and a final oxidative cyclization of the furan ring constitute the key steps of this method. Its utility is exemplified by the first to-tal synthesis of the marine natural product ircinin-4 (2).