A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

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

doi:10.1021/jo500056w

A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

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

Chemistry (Twin Cities)

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11 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4300-4305
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	79
Issue number	10
DOIs	https://doi.org/10.1021/jo500056w
State	Published - May 16 2014

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A convergent approach to the dioxaadamantane core of (±)- tetrodotoxin

Abstract

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