ORGN 676 |
Towards the total synthesis of ficellomycin
| Michael Shipman and David Paumier. School of Chemistry, University of Exeter, Stocker Road, Exeter, EX4 4QD, United Kingdom |
In 1976, Argoudelis et al. described the isolation of ficellomycin from the culture broths of Streptomyces ficellus. This natural product contains a highly strained and unusual 1-azabicyclo[3.1.0]hexane ring system and has been shown to inhibit the in vitro growth of gram positive bacteria and Staphylococcus aureus infections in mice. To date, no studies relating to the synthesis of this antibiotic have been described. This presentation will describe the development of a short, stereoselective route to the 1-azabicyclo[3.1.0]hexane ring system of ficellomycin and further progress towards the total synthesis of this natural product. The key step in our approach involves an intramolecular conjugate addition of an in situ formed aziridine onto a dehydroamino acid. |
| |
|
|