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

Lago-Santomé, Hugo; Meana-Pañeda, Rubén; Alonso, Ricardo

doi:10.1021/jo500056w.s001

jo500056w_si_001.pdf (5.38 MB)

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

journal contribution

posted on 2014-05-16, 00:00 authored 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.