An Efficient Synthesis of Aldohexose-derived Piperidine Nitrones: Precursors of Piperidine Iminosugars
Overview
Authors
Affiliations
Affiliations
Soon will be listed here.
Abstract
D-glucopyranose-derived and L-idopyranose-derived piperidine nitrones were synthesized in good overall yields through six-step reaction sequence starting from readily available 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The method is efficient and could be general for the synthesis of aldohexose-derived piperidine nitrones which are precursors of piperidine iminosugars.
References
1.
Desvergnes S, Py S, Vallee Y
. Total synthesis of (+)-hyacinthacine A2 based on SmI2-induced nitrone umpolung. J Org Chem. 2005; 70(4):1459-62.
DOI: 10.1021/jo048237r.
View
2.
Zhang Z, Nakagawa S, Kato A, Jia Y, Hu X, Yu C
. A concise stereoselective synthesis of (-)-erycibelline. Org Biomol Chem. 2011; 9(22):7713-9.
DOI: 10.1039/c1ob06244a.
View
3.
Goti A, Cacciarini M, Cardona F, Cordero F, Brandi A
. Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide. Org Lett. 2001; 3(9):1367-9.
DOI: 10.1021/ol015747o.
View
4.
Tsou E, Chen S, Yang M, Wang S, Cheng T, Cheng W
. Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library. Bioorg Med Chem. 2008; 16(24):10198-204.
DOI: 10.1016/j.bmc.2008.10.063.
View
5.
Deschamp J, Mondon M, Nakagawa S, Kato A, Alonzi D, Butters T
. Towards a stable noeuromycin analog with a D-manno configuration: synthesis and glycosidase inhibition of D-manno-like tri- and tetrahydroxylated azepanes. Bioorg Med Chem. 2010; 20(2):641-9.
DOI: 10.1016/j.bmc.2010.09.053.
View