Elaboration of the Pyridine C-Ring Functionality in a Streptonigrin Precursor

Deukjoon Kim, Steven M. Weinreb

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Model studies directed toward total synthesis of streptonigrin (1) are outlined. A number of attempts to introduce a 3-amino substituent into compounds 6 and 18, prepared previously by Diels-Alder reactions, are described. A successful method for introduction of this substituent into a preformed pyridine via introduction of a functionalized carbon followed by Curtius rearrangement has been developed. Compound 52 has been prepared which contains all of the features present in the pyridine C ring of streptonigrin synthon 3.

Original languageEnglish (US)
Pages (from-to)125-131
Number of pages7
JournalJournal of Organic Chemistry
Volume43
Issue number1
DOIs
StatePublished - Jan 1 1978

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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