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A Convergent Approach to the Dioxaadamantane Core of (±)-Tetrodotoxin

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journal contribution
posted on 16.05.2014, 00:00 by Hugo Lago-Santomé, Rubén Meana-Pañeda, Ricardo Alonso
A fully stereocontrolled 1,3-diol orthoesterification and a water-promoted intramolecular Henry addition, combined with the previously reported formal (3 + 3) annulation of α-nitro-α,β-enals and 2,2-dimethyl-1,3-dioxan-5-one, provided for a short convergent pathway to the dioxaadamantane core of (±)-tetrodotoxin.