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

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

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 (±)...

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Veröffentlicht in:Journal of organic chemistry 2014-05, Vol.79 (10), p.4300-4305
Hauptverfasser: Lago-Santomé, Hugo, Meana-Pañeda, Rubén, Alonso, Ricardo
Format: Artikel
Sprache:eng
Schlagworte:
Adamantane - chemical synthesis
Adamantane - chemistry
Dioxanes - chemical synthesis
Dioxanes - chemistry
Stereoisomerism
Tetrodotoxin - chemical synthesis
Tetrodotoxin - chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500056w