Total Synthesis of Atrachinenins A and B
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(Accepted version)
Date
2022
Authors
French, S.A.
Sumby, C.J.
Huang, D.M.
George, J.H.
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Journal of the American Chemical Society, 2022; 144(50):22844-22849
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Sarah A. French, Christopher J. Sumby, David M. Huang, and Jonathan H. George
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Abstract
Inspired by a new biosynthetic hypothesis, we report a biomimetic total synthesis of atrachinenins A and B that explains their racemic nature. The synthesis exploits an intermolecular Diels−Alder reaction between a quinone meroterpenoid and E-β-ocimene, followed by intramolecular (3 + 2) cycloaddition and a late-stage aerobic oxidation. Divergent transformations of a simple model system gave several complex polycyclic scaffolds, while also suggesting a structure revision for atrachinenin C.
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© 2022 American Chemical Society