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

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

Research output: Contribution to journalArticlepeer-review

19 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 languageEnglish (US)
Pages (from-to)4773-4779
Number of pages7
JournalJournal of Organic Chemistry
Volume53
Issue number20
DOIs
StatePublished - Sep 1 1988

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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