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Organic Letters
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Article . 2013
License: CC BY
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Organic Letters
Article . 2013 . Peer-reviewed
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Organic Letters
Article . 2014
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One-pot Synthesis of the Tetracyclic Framework of the Aromatic Erythrina Alkaloids from Simple Furans

Authors: Kalaitzakis; D.; Montagnon; T.; Antonatou; E.; Vassilikogiannakis; G.;

One-pot Synthesis of the Tetracyclic Framework of the Aromatic Erythrina Alkaloids from Simple Furans

Abstract

Conversion of a simple furan into the intact erythrinane skeleton in one synthetic operation has been accomplished. The one-pot reaction sequence begins with singlet oxygen photooxygenation of the furan and proceeds via a 2-pyrrolidinone formation, cyclization of the pendant aldehyde moiety and an N-acyliminium ion formation and terminates with a Pictet-Spengler-type aromatic substitution. The method has been used to achieve a rapid and highly effective formal synthesis of erysotramidine.

Keywords

Pictet-Spengler, Molecular Structure, Singlet oxygen, Erysotramidine, Stereoisomerism, Heterocyclic Compounds, 4 or More Rings, Pyrrolidinones, Erythrina Alkaloids, Alkaloids, Cyclization, Furans, Erythrina

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selected citations
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This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
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