Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereoisomeric 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.
AHOND, ALAIN;ALMOURABIT, ALI;ZURITA, MANUEL BEDOYA;COMMERCON, ALAIN;POTLE+
作者:AHOND, ALAIN、ALMOURABIT, ALI、ZURITA, MANUEL BEDOYA、COMMERCON, ALAIN、POTLE+
DOI:——
日期:——
Synthèse stéréosélective de la girolline
作者:Alain Ahond、Ali Al Mourabit、Manuel Bedoya-Zurita、Richard Heng、Raquel Marques Braga、Christiane Poupat、Pierre Potier
DOI:10.1016/s0040-4020(01)80443-9
日期:1992.1
Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereoisomeric 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.