Synthese Stereoselective de la Girolline

Article abstract of DOI:10.1016/S0040-4020(01)80443-9

Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereomeric derivatives have been separated.The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose : this ose is condensed with formamidine acetate to obtain a 4(5)-<1',2',3'-trihydroxypropyl>-imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.Key Words: girolline synthesis; 2-aminoimidazole; D(-)-arabinose; 4(5)<1',2',3'-trihydroxypropyl>imidazole; rhodium reduction.