Synthetic Approaches to the Quinolinequinone System of Streptonigrin

Satoshi Hibino, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

Model studies directed toward synthesis of the quinolinequinone AB ring system of streptonigrin (1) using approaches based upon Friedlander quinoline synthesis are described. Aldehyde 6 has been prepared from o-vanillin, and several unsuccessful attempts were made to convert it to the model quinolinequinone 36. A successful route to 36 was developed using the o-aminobenzaldehyde 30. Friedlander condensation of 30 with 2-acetylpyridine produced quinoline 31, which can be transformed in a few simple steps to quinolinequinone 36. This last route should be applicable to a total synthesis of streptonigrin.

Original languageEnglish (US)
Pages (from-to)232-236
Number of pages5
JournalJournal of Organic Chemistry
Volume42
Issue number2
DOIs
StatePublished - Jan 1 1977

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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