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Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A

MPS-Authors
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Preindl,  Johannes
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Wirtz,  Cornelia
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lingnau,  Julia
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Citation

Preindl, J., Schulthoff, S., Wirtz, C., Lingnau, J., & Fürstner, A. (2017). Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A. Angewandte Chemie International Edition, 56(26), 7525-7530. doi:10.1002/anie.201702189.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002D-8AED-B
Abstract
Orevactaene and epipyrone A were previously thought to comprise the same polyunsaturated tail but notably different C-glycosylated 4-hydroxy-2-pyrone head groups. Total synthesis now shows that the signature bicyclic framework assigned to orevactaene is a chimera; the compound is almost certainly identical with epipyrone A, whose previously unknown stereochemistry has also been established during this study. Key to success was the ready formation of the bicyclic core of putative orevactaene by a sequence of two alkyne cycloisomerization reactions using tungsten and gold catalysis. Equally important was the flexibility in the assembly process gained by the use of heterobimetallic polyunsaturated modules whose termini could be selectively and consecutively addressed in a practical one-pot cross-coupling sequence.