Efficient synthesis for each of the eight stereoisomers of the iminosugars lentiginosine and 1,4-dideoxy-1,4-imino-D-arabinitol (DAB)

Herein, we describe the efficient, diastereoselective syntheses of the iminosugars 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) 1b, lentiginosine 3a, and the seven stereoisomers of each of these iminosugars starting from 4-benzoyl-6-deoxy-6-iodoglycopyranosides 47 with yields ranging from 38 % to 68 % f...

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Bibliographic Details
Published in:	Carbohydrate research Vol. 545; p. 109280
Main Authors:	Liotta, Louis J., Antoine, Jessica, Brammer Basta, Leighanne A., Campbell, Andrew S., Cole, Gabrielle Y., Demick Brazile, Kristen A., Dogal Gardner, Natalie M., Fitzgerald, Megan E., Francois, Jean E.K., French, Brian M., Garafola, Sara L., Giannetti, Catherine A., Granatosky, Eve A., Harney, Alycen M., Hummel, James T., Joyce, Andrew P., Keylor, Mitchell H., Khubchandani, Jasmine A., Korzeniecki, Claudia, Lieberman, Diana C., Litterio, Joshua M., Maiorano, Madison O., Marshall, Jessica F., McCarthy, Kelly A., Mendes Vieira, Andreia, Miller, Ruby M., Morrison, Emily R., Moura, Steven P., Neumann, Dillon F., Oliveira, Aliza F., Pace, Nicholas J., Plouffe, Jodie X., Pomfret, Meredith N., Reardon, Katelyn N., Sheller-Miller, Samantha M., Smith, Michael J., Sullivan, Jessica L., Sweeney, Samantha W., Tougas, Kerstin L.
Format:	Journal Article
Language:	English
Published:	Netherlands Elsevier Ltd 01-11-2024
Online Access:	Get full text
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Summary:	Herein, we describe the efficient, diastereoselective syntheses of the iminosugars 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) 1b, lentiginosine 3a, and the seven stereoisomers of each of these iminosugars starting from 4-benzoyl-6-deoxy-6-iodoglycopyranosides 47 with yields ranging from 38 % to 68 % for the DAB and isomers 1a-1h and from 44 % to 89 % for the lentiginosine and isomers 3a-3h. We also report the syntheses of the eight stereoisomers of the 4-benzoyl-6-deoxy-6-iodoglycopyranosides 47 from commercially available sugars. Key to the iminosugar syntheses is a single multistep reaction that converts the 4-benzoyl-6-deoxy-6-iodoglycopyranosides 47 to a vinyl pyrrolidine through a one-pot zinc mediated reductive elimination, followed by a reductive amination and finally an intramolecular nucleophilic substitution. Strategic selection of the amine utilized in the reductive amination and the functionalization of the intermediate carbon-carbon double bond provides access to a vast array of iminosugars. [Display omitted] •Efficient, high-yielding, three-step synthesis of iminosugars from common sugars.•Specific control of three contiguous stereocenters in synthesis of iminosugars.•Preparation of all eight stereoisomers of DAB and lentiginosine.•Common sugar to iminosugars, three substantial steps in a one-pot reaction.•Adaptable synthesis for many pyrrolidine containing iminosugars.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0008-6215 1873-426X 1873-426X
DOI:	10.1016/j.carres.2024.109280