The total synthesis of cyanindin-3-glucoside (C3G) appropriate for ��C enrichment at C-1` and C-6` has been achieved for metabolic studies.
Construction of the phenolic ring-B was achieved by a Diels-Alder reaction employing a novel diene, (2R,3R)-2,3-dimethyoxy-2,3-dimethyl-5,6-dimethylene-1,4-dioxane, which incorporates a butane diacetal protecting motif. Reaction with a (labelled) dienophile affords the protected catechol.
Formation of the flavone skeleton was achieved by condensation of the benzamide (ring-B) with an acetophenone (ring-A).
Esterification of the flavone skeleton in ring-A was found to be essential for oxidation at C-3 with dimethyldioxirane affording the flavonol. Glycosylation using a glucosyl bromide gave the β-adduct exclusively which was reduced to the target compound, C3G.
The overall synthetic design permits the synthesis of the labelled anthocyanin in nine steps (23%) from the dienophile.
| Identifer | oai:union.ndltd.org:ADTP/208072 |
| Date | January 2008 |
| Creators | Compton, Benjamin Jason, n/a |
| Publisher | University of Otago. Department of Chemistry |
| Source Sets | Australiasian Digital Theses Program |
| Language | English |
| Detected Language | English |
| Rights | http://policy01.otago.ac.nz/policies/FMPro?-db=policies.fm&-format=viewpolicy.html&-lay=viewpolicy&-sortfield=Title&Type=Academic&-recid=33025&-find), Copyright Benjamin Jason Compton |
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