Synthesis of 1-O-Methyl-β,D-ezoaminuroic Acid

Spencer Knapp; Anthony T. Levorse; Joseph A. Potenza

doi:10.1021/jo00255a020

Synthesis of 1-O-Methyl-β,D-ezoaminuroic Acid

Spencer Knapp, Anthony T. Levorse, Joseph A. Potenza

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20 Scopus citations

Abstract

The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13% overall yield) is described. The key step is a transannular “bromolactamization” reaction, which sets up the stereocontrolled functionalization of the pyran ring. The use of resolved p-methoxyphenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.

Original language	English (US)
Pages (from-to)	4773-4779
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	53
Issue number	20
DOIs	https://doi.org/10.1021/jo00255a020
State	Published - Sep 1 1988

All Science Journal Classification (ASJC) codes

Organic Chemistry

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abstract = "The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13% overall yield) is described. The key step is a transannular “bromolactamization” reaction, which sets up the stereocontrolled functionalization of the pyran ring. The use of resolved p-methoxyphenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.",

author = "Spencer Knapp and Levorse, {Anthony T.} and Potenza, {Joseph A.}",

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T1 - Synthesis of 1-O-Methyl-β,D-ezoaminuroic Acid

AU - Knapp, Spencer

AU - Levorse, Anthony T.

AU - Potenza, Joseph A.

PY - 1988/9/1

Y1 - 1988/9/1

N2 - The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13% overall yield) is described. The key step is a transannular “bromolactamization” reaction, which sets up the stereocontrolled functionalization of the pyran ring. The use of resolved p-methoxyphenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.

AB - The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13% overall yield) is described. The key step is a transannular “bromolactamization” reaction, which sets up the stereocontrolled functionalization of the pyran ring. The use of resolved p-methoxyphenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.

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JF - Journal of Organic Chemistry

IS - 20

ER -

Synthesis of 1-O-Methyl-β,D-ezoaminuroic Acid

Abstract

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