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Journal Article

Exploiting the Reversibility of Olefin Metathesis. Syntheses of Macrocyclic Trisubstituted Alkenes and (R,R)-(−)-Pyrenophorin

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

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Thiel,  Oliver R.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Citation

Fürstner, A., Thiel, O. R., & Ackermann, L. (2001). Exploiting the Reversibility of Olefin Metathesis. Syntheses of Macrocyclic Trisubstituted Alkenes and (R,R)-(−)-Pyrenophorin. Organic Letters, 3(3), 449-451. doi:10.1021/ol0069554.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-34CC-B
Abstract
The formation of the trisubstituted cycloalkene 7 by RCM of diene 5 proceeds via the acyclic dimer 6, thus demonstrating the ready reversibility of olefin metathesis if catalyzed by “second generation” ruthenium carbene complexes such as 2−4. When applied to acrylate 11, these catalysts trigger a cyclooligomerization process that evolves with time and serves as key step en route to the lactide antibiotic (−)-pyrenophorin 8.