A concise total synthesis of unprecedented tetranorsesquiterpenoids applanatumol Z5

A unified approach to meroterpenoids applanatumols B, V, W, X, and Y produced by the medicinal fungus Ganoderma applanatum and 2′-epi-spiroapplanatumine O is presented. The key synthetic sequence consists of a tandem anionic ketone allylation/oxy-Cope rearrangement/α-oxygenation furnishing an α-aminoxy ketone and a persistent radical effectbased 5-exo-trig cyclization leading to the trisubstituted cyclopentane core. The relative configuration of applanatumol V has to be revised. Some compounds display significant cytotoxic and antioxidant properties.

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Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum

Šimek

Bártová

Issad

et al. 2022

Org. Lett.

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Total synthesis of applanatumol A

et al. 2023

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A concise total synthesis of unprecedented tetranorsesquiterpenoids applanatumol Z5

Cited by 2 publications

References 40 publications

Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum

Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum

Total synthesis of applanatumol A

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