Total syntheses of (±)-β-erythroidine and (±)-8-oxo- β-erythroidine by an intramolecular Diels-Alder cycloaddition of a 2-amidoacrolein

Yong He; Raymond L. Funk

doi:10.1021/ol061267r

Total syntheses of (±)-β-erythroidine and (±)-8-oxo- β-erythroidine by an intramolecular Diels-Alder cycloaddition of a 2-amidoacrolein

Yong He, Raymond L. Funk

Chemistry

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26 Scopus citations

Abstract

The total syntheses of (±)-β-erythroidine and (±)-8-oxo-β-erythroidine are described. The tetracyclic ring system of the natural products was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of an amidodioxin, an intramolecular Heck reaction, and a 6π-electrocyclic ring closure of a dienoic acid.

Original language	English (US)
Pages (from-to)	3689-3692
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	17
DOIs	https://doi.org/10.1021/ol061267r
State	Published - Aug 17 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol061267r

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AB - The total syntheses of (±)-β-erythroidine and (±)-8-oxo-β-erythroidine are described. The tetracyclic ring system of the natural products was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of an amidodioxin, an intramolecular Heck reaction, and a 6π-electrocyclic ring closure of a dienoic acid.

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Total syntheses of (±)-β-erythroidine and (±)-8-oxo- β-erythroidine by an intramolecular Diels-Alder cycloaddition of a 2-amidoacrolein

Abstract

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