Total synthesis of rhodonoids A B, E, and F, enabled by singlet oxygen ene reactions

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2020

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Burchill, L.
George, J.H.

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Journal article

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Journal of Organic Chemistry, 2020; 85(4):2260-2265

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Laura Burchill and Jonathan H. George

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Abstract

Singlet oxygen is a versatile reagent for the selective oxidation of organic compounds under mild reaction conditions. It is frequently invoked in biosynthetic pathways, so it is especially suitable for application in the biomimetic synthesis of natural products. Herein, we show that use of the singlet oxygen ene reaction, combined with [2 + 2] cycloadditions, leads to concise, divergent, and redox-economic total syntheses of several polycyclic members of the rhodonoid family of meroterpenoids.

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© 2020 American Chemical Society

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