Asymmetric synthesis of novel isoindolines: azasaccharide mimics as potential enzyme inhibitors.
2',3'-Dideoxy-2',3'-didehydronucleosides and azasaccharides are known to possess antiviral activity. The synthesized 1-methoxyisoindoline system (10), which is related to the above nucleosides, is potentially stable in-vivo. The 1-methoxyisoindoline was synthesized from the achiral phthalaldehyde in 10 steps via an enantiomerically pure diol obtained by Sharpless asymmetric dihydroxylation. The new heterocyclic compound is an azosaccharide mimic which provides an access to a new series of nucleoside analogues with potential as antiretroviral agents (anti-HIV) and as glycosidase inhibitors.
Ewing
D F
DF
Department of Chemistry, University of Hull, UK.
Len
C
C
Mackenzie
G
G
Petit
J P
JP
Ronco
G
G
Villa
P
P
D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*
D015224:Dideoxynucleosides; D004791:Enzyme Inhibitors; D007211:Indoles; C057812:indoline