Synthesis of eupolauridine and its benzo-annulated derivative

Article abstract of DOI:10.1080/00397919208020497

The unique diazafluoranthene alkaloid eupolauridine (1) was synthesized by a three-step routine utilizing as the initial step the thermal rearrangement of the oxime O-crotyl ether 12, which afforded onychine (2). Bracher pyridine synthesis procedure subsequently converted 2 into 1. On the other hand, Friedlander reaction was employed for the synthesis of 3, which is a benzo-annulated derivative of eupolauridine (1).