Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D. (2nd May 2018)

• Record Type: Journal Article
• Authors: Yan, Shiqiang; Ren, Sumei; Ding, Ning; Li, Yingxia
• Is Part Of: Carbohydrate research. Volume 460(2018)
• Page Start: 41
• Page End: 46
• Publication Date: 2018-05-02
• Subjects: Acylated phenolic glycosides -- Vitexnegheteroin A -- Ovatoside D -- Regioselective acylation; 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.2018.02.015
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O -6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3 -NaBH4 system in one pot. Graphical abstract: Highlights: The first total synthesis of vitexnegheteroin A and ovatoside D. Short reaction steps (only 4 steps). High overall yields (54% and 65% respectively).