Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/15530
Title: Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes
Contributor(s): Stockton, Kieran (author); Greatrex, Ben  (author)orcid ; Taylor, Dennis K (author)
Publication Date: 2014
DOI: 10.1021/jo500645z
Handle Link: https://hdl.handle.net/1959.11/15530
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-alkyldialdoses 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.
Publication Type: Journal Article
Source of Publication: Journal of Organic Chemistry, 79(11), p. 5088-5096
Publisher: American Chemical Society
Place of Publication: United States of America
ISSN: 1520-6904
0022-3263
Field of Research (FOR): 030503 Organic Chemical Synthesis
030502 Natural Products Chemistry
Socio-Economic Outcome Codes: 970103 Expanding Knowledge in the Chemical Sciences
860899 Human Pharmaceutical Products not elsewhere classified
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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