Highly functionalized cyclopentanes from meso bicyclic hydrazines. A rapid access to mannosidase inhibitors.
A simple diastereoselective access to amino- and hydrazinocyclopentitols is described. The key step involves a cationic rearrangement of a meso bicyclic hydrazine, followed by two successive stereoselective hydroxylations. Both racemic compounds are micromolar alpha-mannosidase (Jack bean) inhibitors.
Bournaud
C
C
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l'Observatoire, 75270 Paris Cedex 06, France.
Robic
D
D
Bonin
M
M
Micouin
L
L
D020650:Combinatorial Chemistry Techniques; D003517:Cyclopentanes / Q000032:analysis / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000032:analysis / Q000138:chemical synthesis*; D006834:Hydrazines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors*
D003517:Cyclopentanes; D004791:Enzyme Inhibitors; D006834:Hydrazines; C060107:mannostatin A; D043323:alpha-Mannosidase