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-Reference-Cited by-同舟云学术

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

Published:2021-09-21 Issue:20 Volume:32 Page:2046-2052
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Ohmori Ken¹^ORCID,Suzuki Keisuke¹^ORCID,Matsuoka Seiya¹,Azami Kohei¹,Fujiki Yusuke¹,Dohi Reina¹,Yasuike Tomokazu²³

Affiliation:

1. Department of Chemistry, Tokyo Institute of Technology

2. Department of Liberal Arts, The Open University of Japan

3. Elements Strategy Initiative for Catalysis and Batteries, Kyoto University

Abstract

AbstractWe 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.

Funder

Nagase Science Technology Foundation

Japan Society for the Promotion of Science

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1719836.pdf

Reference5 articles.

1. Total Synthesis of Carthamin, a Traditional Natural Red Pigment

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4. Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

5. Inductive Effects on the Acid Dissociation Constants of Mercaptans1

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