ol990880q_si_003.tif (730.59 kB)
Variable Strategy toward Carbasugars and Relatives As Illustrated by Diastereoselective Synthesis of 1-Deoxy-1-amino-pseudo-β-d-gulopyranose (Alias 1,2,4-Tri-epi-validamine)
figure
posted on 1999-09-23, 00:00 authored by Gloria Rassu, Luciana Auzzas, Luigi Pinna, Franca Zanardi, Lucia Battistini, Giovanni CasiraghiA quick arrival at chiral nonracemic cyclohexanoids is provided, which incorporates useful variability for large product diversity. Central to
the construction is the exploitation of the dual nucleophilic character of an easily accessible triad of silyloxy diene synthons derived from the
popular five-membered heterocycles furan, pyrrole, and thiophene. To assess the reliability of the procedure, the total synthesis of 1-deoxy-1-amino-pseudo-β-d-gulopyranose (10) (alias 1,2,4-tri-epi-validamine) is executed, in 12 steps and with a 17% overall yield, by starting with
N-tert-butoxycarbonyl-2-[(tert-butyldimethylsilyl)oxy]pyrrole (1) and 2,3-O-isopropylidene-d-glyceraldehyde (2).
History
Usage metrics
Keywords
Trifuranvalidaminepyrrolereliabilitysilyloxy diene synthonsnucleophilic characterCentralDiastereoselective Synthesisbutoxycarbonylchiral nonracemic cyclohexanoidsDeoxyheterocyclethiophene12 stepsCarbasugardeoxyarrivalvariabilitytertVariable StrategyAliaconstructionproduct diversitytriexploitationIllustratedaliasbutyldimethylsilylepitriadsynthesisprocedure
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC