Unified Total Synthesis of Diverse Meroterpenoids from Ganoderma Applanatum

• DOI: 10.1021/acs.orglett.2c01633
• Publication Date: 2022-06-19T11:43:51Z
• Authors: Michal Šimek; Kateřina Bártová; Samy Issad; Miroslav Hájek; Ivana Císařová; Ullrich Jahn
• Keywords: Cyclopentanes; Tandem; Terpene

A unified approach to meroterpenoids applanatumols B, V, W, X, and Y produced by the medicinal fungus Ganoderma applanatum 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 persistent radical effect-based 5-exo-trig cyclization leading trisubstituted cyclopentane core. relative configuration applanatumol V has be revised. Some compounds display significant cytotoxic antioxidant properties.