Stereoselective synthesis of (+)-1-deoxyaltronojirimycin

被引:2
作者
Righi, Giuliana [1 ]
Mandic, Emanuela [2 ]
Tirotta, Ilaria [2 ]
Naponiello, Gaia Clara Mercedes [2 ]
Sappino, Carla [2 ]
Marucci, Cristina [2 ]
Tomei, Michela [2 ]
Bovicelli, Paolo [1 ]
机构
[1] Univ Roma La Sapienza, CNR IBPM, Dept Chem, Rome, Italy
[2] Univ Roma La Sapienza, Dept Chem, Rome, Italy
关键词
Iminosugar; stereoselective synthesis; heterocycles; dihydroxylation; 1-deoxyaltronojirimycin; ASYMMETRIC-SYNTHESIS; 1-DEOXYNOJIRIMYCIN; ACID; 1-DEOXYALTRONOJIRIMYCIN; DIHYDROXYLATION; TRANSFORMATIONS; DERIVATIVES; OXIDATION; ANALOGS; ESTER;
D O I
10.1080/14786419.2015.1131983
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A stereocontrolled, facile and high-yield approach for producing (+)-altroDNJ, has been developed starting from the inexpensive commercial cis 2-butene-1,4-diol. Sharpless epoxidation and a subsequent dihydroxylation were used for the introduction of all stereocentres; finally, the ring closure under basic conditions afforded the piperidine heterocycle. [GRAPHICS] .
引用
收藏
页码:1655 / 1660
页数:6
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