Synthetic Study on Carthamin, Part 4. Improved Synthesis of a C-Glycosyl Quinochalcone by Installation of a Side Chain through Regioselective De-O-methylation and Acyl Rearrangement

Abstract We report an improved synthesis of a C -Glycosyl quinochalcone that is a key intermediate in our total synthesis of carthamin, a natural red pigment of traditional heritage. The C -glycosyl quinochalcone is prepared by regioselective de- O -methylation of a C -glycosyl bromodienone, and ins...

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Published in:Synlett 2021-12, Vol.32 (20), p.2046-2052
Main Authors: Matsuoka, Seiya, Azami, Kohei, Fujiki, Yusuke, Dohi, Reina, Yasuike, Tomokazu, Ohmori, Ken, Suzuki, Keisuke
Format: Article
Language:English
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Summary:Abstract We report an improved synthesis of a C -Glycosyl quinochalcone that is a key intermediate in our total synthesis of carthamin, a natural red pigment of traditional heritage. The C -glycosyl quinochalcone is prepared by regioselective de- O -methylation of a C -glycosyl bromodienone, and installation of a p -coumaroyl side chain through an O → C acyl rearrangement.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1719836