Total synthesis confirms the unique structure of alanense B, highlighting enolate alkylation and diastereoselectivity in its synthesis.
A total synthesis of (±)-alanense B, a unique and unprecedented 2-aryl substituted cadinane-type sesquiterpenoid that exhibits spontaneous calcium channel oscillations in primary cultured neocortical neurons, has been accomplished. Intramolecular Friedel-Crafts acylation and enolate methylation using KHMDS in 1,2-dimethoxyethane yielded the pentasubstituted 1-tetralone bearing a quaternary stereogenic center at the C2 position with complete diastereoselectivity. Cleavage of three phenolic methyl ethers prior to DDQ oxidation was essential for reaching the final product.
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Matsumoto et al. (2025) studied this question.
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