Oxidation of 3,5-di-C-(per-O-acetylglucopyranosyl)phloroacetophenone in the synthesis of hydroxysafflor yellow A

Toshiyuki Suzuki; Mitsuo Ishida; Toshihiro Kumazawa; Shingo Sato

doi:10.1016/j.carres.2017.05.009

Oxidation of 3,5-di-C-(per-O-acetylglucopyranosyl)phloroacetophenone in the synthesis of hydroxysafflor yellow A

Carbohydr Res. 2017 Aug 7:448:52-56. doi: 10.1016/j.carres.2017.05.009. Epub 2017 May 13.

Authors

Toshiyuki Suzuki¹, Mitsuo Ishida¹, Toshihiro Kumazawa¹, Shingo Sato²

Affiliations

¹ Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan.
² Graduate School of Science and Engineering, Yamagata University, Jonan 4-3-16, Yonezawa-shi, Yamagata 992-8510, Japan. Electronic address: shingo-s@yz.yamagata-u.ac.jp.

PMID: 28601672
DOI: 10.1016/j.carres.2017.05.009

Abstract

In the synthesis of the main yellow pigment hydroxysafflor yellow A (HSYA), that is present in safflower petals, the key compound 4-(S)-2-acetyl-4,6-di-C-(per-O-acetyl-β-D-glucosyl)-3,4-dihydroxy-5-methoxycyclohexa-2,5-dienone (11b) was diastereoselectively synthesized in an overall yield of 18% from di-C-β-D-glucosylphloroacetophenone per-O-acetate (8).

Keywords: C-glycosylquinochalcone; Diastereoselectivity; Hydroxysafflor yellow A; Intramolecular condensation; Oxidation; Safflower petal.

MeSH terms

Acetophenones / chemistry*
Chalcone / analogs & derivatives*
Chalcone / chemical synthesis
Chalcone / chemistry
Chemistry Techniques, Synthetic
Monosaccharides / chemistry*
Oxidation-Reduction
Quinones / chemical synthesis*
Quinones / chemistry*

Substances

Acetophenones
Monosaccharides
Quinones
hydroxysafflor yellow A
Chalcone