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Racemic Total Synthesis of Elmonin and Pratenone A, from Streptomyces, Using a Common Intermediate Prepared by peri-Directed C–H Functionalization

The first total synthesis of elmonin and pratenone A, two complex rearranged angucyclinones from Streptomyces, is reported. Using peri-directed C–H functionalization, the key naphthalene fragment present in both synthetic targets… Click to show full abstract

The first total synthesis of elmonin and pratenone A, two complex rearranged angucyclinones from Streptomyces, is reported. Using peri-directed C–H functionalization, the key naphthalene fragment present in both synthetic targets was efficiently prepared. Coupling to two anisole-derived fragments gave access to the natural products, in which elmonin was prepared using a biomimetic spiro-ketalization.

Keywords: directed functionalization; elmonin pratenone; total synthesis; peri directed; synthesis elmonin

Journal Title: Organic Letters
Year Published: 2022

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