Progress toward the synthesis of (Z)-axinohydantoin and (Z)- debromoaxinohydantoin

ORGN 778

Gianluca M. E. Papeo, gianluca.papeo@nervianoms.com, Federico Tutino, Helena Posteri, Francesca Quartieri, and Nicola Mongelli. Chemistry, Nerviano Medical Sciences, Viale Pasteur 10, Nerviano (Milano), 20014, Italy
(Z)-Axinohydantoin (1) and (Z)-debromoaxinohydantoin (2), isolated from the marine sponges Stylotella Aurantium and Monachora Hymeniacidon, proved to possess moderate activities in inhibiting the progress of the cell cycle at different phases. While (Z)-axinohydantoin (1) did not succumb to total synthesis so far, an elegant approach to (Z)-debromoaxinohydantoin (2) has been reported by Horne. In trying to access axinohydantoins (Figure 1), we envisioned to capitalize on 1-benzoyl-2-methylsulfanyl-1,5-dihydroimidazol-4-one (3), a reagent developed in our laboratories for the construction of the north ring in hymenialdisines. Progress of our efforts will be presented.

Figure 1. Planned Strategy Towards Axinohydantoins (1) and (2)

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007