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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry