Oxidation of 3, 5-di-C-(per-O-acetylglucopyranosyl)phloroacetophenone in the synthesis of hydroxysafflor yellow A. (7th August 2017)

• Record Type: Journal Article
• Authors: Suzuki, Toshiyuki; Ishida, Mitsuo; Kumazawa, Toshihiro; Sato, Shingo
• Is Part Of: Carbohydrate research. Volume 448(2017)
• Page Start: 52
• Page End: 56
• Publication Date: 2017-08-07
• Subjects: Safflower petal -- Hydroxysafflor yellow A -- C-glycosylquinochalcone -- Intramolecular condensation -- Oxidation -- Diastereoselectivity; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2017.05.009
• Languages: English
• ISSNs: 0008-6215

Abstract

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 ). Graphical abstract: Highlights: The structure of the main yellow component in safflower petals has been discussed. The compound di- C -glycoside HSYA undergoes an intramolecular condensation. A key compound in the synthesis of HSYA is a 4-( S )-di- C -glucosylquinol. 4-( S )-di- C -glucosylquinol was synthesized via diastereoselective oxidation. Configuration of the new stereocenter was determined by circular dichroism.