STEREOSELECTIVE SYNTHESIS OF GIROLLINE

被引：12

作者：

AHOND, A ^{[1
]}

ALMOURABIT, A ^{[1
]}

BEDOYAZURITA, M ^{[1
]}

HENG, R ^{[1
]}

BRAGA, RM ^{[1
]}

POUPAT, C ^{[1
]}

POTIER, P ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON | 1992年 / 48卷 / 21期

关键词：

GIROLLINE SYNTHESIS; 2-AMINOIMIDAZOLE; D(-)ARABINOSE; 4(5)[1'; 2'; 3'-TRIHYDROXYPROPYL]IMIDAZOLE; RHODIUM REDUCTION;

D O I：

10.1016/S0040-4020(01)80443-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4327 / 4346

页数：20

共 14 条

[1]

ALMOURABIT A, 1989, THESIS U PARIS SUD

[2]

ALMOURABIT A, 1991, 3E S SUBST NAT INT R

[3]

AMES BN, 1957, J BIOL CHEM, V228, P131

[4]

AMES BN, 1955, J BIOL CHEM, V212, P687