Synlett 2021; 32(20): 2046-2052
DOI: 10.1055/s-0040-1719836
letter

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

Seiya Matsuoka
a   Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
,
Kohei Azami
a   Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
,
Yusuke Fujiki
a   Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
,
Reina Dohi
a   Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
,
Tomokazu Yasuike
b   Department of Liberal Arts, The Open University of Japan, 2-11 Wakaba, Mihama-ku, Chiba 261-8586, Japan
c   Elements Strategy Initiative for Catalysis and Batteries, Kyoto University, 1-30 Goryo-Ohara, Nishikyo-ku, Kyoto 615-8520, Japan
,
Ken Ohmori
a   Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
,
a   Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
› Institutsangaben

This work was supported by Grants-in-Aid from the Japan Society for the Promotion of Science (JSPS) (Grants JP16H06351, JP16H04107, JP18H04391, JP21H04703) and by the Nagase Science Technology Foundation.


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In memory of the late Professor Daisuke Uemura.

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 OC acyl rearrangement.

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Publikationsverlauf

Eingereicht: 02. August 2021

Angenommen nach Revision: 20. August 2021

Artikel online veröffentlicht:
21. September 2021

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