111765-92-5Relevant academic research and scientific papers
A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars
Harit, Vimal Kant,Ramesh, Namakkal G.
, (2020/05/08)
A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-D-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-L-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields.
A new approach to (+)-anisomycin
Santhosh Reddy,Ravi Kumar,Venkateswara Rao
, p. 3154 - 3159 (2007/10/03)
An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.
AN ASYMMETRIC TOTAL SYNTHESIS OF UNNATURAL (+)-ANISOMYCIN
Meyers, A. I.,Dupre, Brian
, p. 113 - 116 (2007/10/02)
Utilizing the valine-based chiral formamidine of 2,5-dihydropyrrole, enantioselective alkylation with p-methoxybenzyl chloride gave, after several subseguent synthetic manipulations, the unnatural enantiomer, (+)-anisomycin, in 22percent overall yield and
