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Type: Journal article
Title: Synthesis of allo-and epi-inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes
Author: Stockton, K.
Greatrex, B.
Taylor, D.
Citation: Journal of Organic Chemistry, 2014; 79(11):5088-5096
Publisher: American Chemical Society
Issue Date: 2014
ISSN: 0022-3263
Statement of
Kieran P. Stockton, Ben W. Greatrex, and Dennis K. Taylor
Abstract: A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.
Rights: © 2014 American Chemical Society
DOI: 10.1021/jo500645z
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