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Total Synthesis of Neurymenolide A Based on a Gold-Catalyzed Synthesis of 4-Hydroxy-2-pyrones

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

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Corbet,  Matthieu
Research Department Fürstner, 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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Chaładaj, W., Corbet, M., & Fürstner, A. (2012). Total Synthesis of Neurymenolide A Based on a Gold-Catalyzed Synthesis of 4-Hydroxy-2-pyrones. Angewandte Chemie International Edition, 51(28), 6929-6933. doi:10.1002/anie.201203180.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-F0C7-2
Abstract
Treat me gently: For a selective synthesis of the unusually sensitive cyclophanic α-pyrone neurymenolide A, the chosen catalysts must be able to distinguish between six different sites of unsaturation, without scrambling any of the skipped π systems. This challenge was met with a new gold-catalyzed pyrone synthesis in combination with a molybdenum-catalyzed ring-closing alkyne metathesis.