Synthesis of C-Ring Functionalized Phenanthridines employing Intramolecular Diels-Alder of Furan (IMDAF) as the Key Step

Abstract

A synthetic strategy towards the (aza)phenanthridine ring-system (3) employing an intramolecular Diels-Alder of furan (IMDAF) as the key step, has previously been developed in our research group (Scheme 1). The exploration of this synthetic pathway has until now been focused on substitution in the phenanthridine A-ring. Herein is described the synthesis of (partly reduced) phenanthridines functionalized in the C-ring by employing a substituted allylic moiety, and by selective ringopening of the intramolecular Diels-Alder adduct 7 (Scheme 2).

A synthetic strategy towards the (aza)phenanthridine ring-system (3) employing an intramolecular Diels-Alder of furan (IMDAF) as the key step, has previously been developed in our research group (Scheme 1). The exploration of this synthetic pathway has until now been focused on substitution in the phenanthridine A-ring. Herein is described the synthesis of (partly reduced) phenanthridines functionalized in the C-ring by employing a substituted allylic moiety, and by selective ringopening of the intramolecular Diels-Alder adduct 7 (Scheme 2).