New synthetic reactions: Applications to discorhabdins and carbacephems
Ciufolini, Marco A.
Doctor of Philosophy
A novel approach for the synthesis of antitumor agents Discorhabdins (1) is described. The synthetic route features a new Paterno-Buchi photo reaction for the spirocyclic ring preparation and cascade Michael reactions for the construction of pyrrolidine unit. The preparation of an advanced intermediate (2) will be discussed.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) A parallel investigation deals with the application of an Aza-Achmatowicz rearrangement for the synthesis of carbacephems. Both cis and trans series of bicyclic $\beta$-lactams were easily available through the Aza-Achmatowicz sequence.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)
Organic chemistry; Pharmaceutical chemistry